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Efficient Organocatalytic Construction of C4-Alkyl Substituted Piperidines and Their Application to the Synthesis of (+)-α-Skytanthine.

Chemistry (Weinheim an der Bergstrasse, Germany)

Shiomi S, Sugahara E, Ishikawa H.
PMID: 26333476
Chemistry. 2015 Oct 12;21(42):14758-63. doi: 10.1002/chem.201503117. Epub 2015 Sep 03.

Chiral piperidines which contain an alkyl group at C4 positions are one of the important architectures because it is appeared in several natural products. An efficient protocol for the preparation of C4-alkyl substituted chiral piperidines using secondary amine catalyzed...

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Shiomi S, Sugahara E, Ishikawa H. Efficient Organocatalytic Construction of C4-Alkyl Substituted Piperidines and Their Application to the Synthesis of (+)-α-Skytanthine. Chemistry. 2015;21(42):14758-63doi: 10.1002/chem.201503117.
Shiomi, S., Sugahara, E., & Ishikawa, H. (2015). Efficient Organocatalytic Construction of C4-Alkyl Substituted Piperidines and Their Application to the Synthesis of (+)-α-Skytanthine. Chemistry (Weinheim an der Bergstrasse, Germany), 21(42), 14758-63. https://doi.org/10.1002/chem.201503117
Shiomi, Shinya, et al. "Efficient Organocatalytic Construction of C4-Alkyl Substituted Piperidines and Their Application to the Synthesis of (+)-α-Skytanthine." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,42 (2015): 14758-63. doi: https://doi.org/10.1002/chem.201503117
Shiomi S, Sugahara E, Ishikawa H. Efficient Organocatalytic Construction of C4-Alkyl Substituted Piperidines and Their Application to the Synthesis of (+)-α-Skytanthine. Chemistry. 2015 Oct 12;21(42):14758-63. doi: 10.1002/chem.201503117. Epub 2015 Sep 03. PMID: 26333476.
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Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines.

Organic & biomolecular chemistry

Kim YR, Hall DG.
PMID: 27143333
Org Biomol Chem. 2016 May 18;14(20):4739-48. doi: 10.1039/c6ob00685j.

The development of new, efficient and economical methods for the preparation of functionalized, optically enriched piperidines is important in the field of drug discovery where this class of heterocycles is often deemed a privileged structure. We have optimized a...

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Kim YR, Hall DG. Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines. Org Biomol Chem. 2016;14(20):4739-48doi: 10.1039/c6ob00685j.
Kim, Y. R., & Hall, D. G. (2016). Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines. Organic & biomolecular chemistry, 14(20), 4739-48. https://doi.org/10.1039/c6ob00685j
Kim, You-Ri, and Hall, Dennis G. "Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines." Organic & biomolecular chemistry vol. 14,20 (2016): 4739-48. doi: https://doi.org/10.1039/c6ob00685j
Kim YR, Hall DG. Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines. Org Biomol Chem. 2016 May 18;14(20):4739-48. doi: 10.1039/c6ob00685j. PMID: 27143333.
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Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes.

Journal of the American Chemical Society

Chen C, Chen P, Liu G.
PMID: 26636720
J Am Chem Soc. 2015 Dec 23;137(50):15648-51. doi: 10.1021/jacs.5b10971. Epub 2015 Dec 10.

The first catalytic trifluoromethoxylation of unactivated alkenes has been developed, in which Pd(CH3CN)2Cl2 was used as catalyst, AgOCF3 as trifluoromethoxide source, and Selectfluor-BF4 as oxidant. A variety of 3-OCF3 substituted piperidines were selectively obtained in good yields. Direct evidence...

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Chen C, Chen P, Liu G. Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes. J Am Chem Soc. 2015;137(50):15648-51doi: 10.1021/jacs.5b10971.
Chen, C., Chen, P., & Liu, G. (2015). Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes. Journal of the American Chemical Society, 137(50), 15648-51. https://doi.org/10.1021/jacs.5b10971
Chen, Chaohuang, et al. "Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes." Journal of the American Chemical Society vol. 137,50 (2015): 15648-51. doi: https://doi.org/10.1021/jacs.5b10971
Chen C, Chen P, Liu G. Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes. J Am Chem Soc. 2015 Dec 23;137(50):15648-51. doi: 10.1021/jacs.5b10971. Epub 2015 Dec 10. PMID: 26636720.
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A Pd-Catalyzed Synthesis of Functionalized Piperidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Allen BD, Connolly MJ, Harrity JP.
PMID: 27273202
Chemistry. 2016 Sep 05;22(37):13000-3. doi: 10.1002/chem.201602586. Epub 2016 Jul 05.

A readily available cyclic carbamate 1 functions as a general precursor to a range of functionalized piperidine products via a new Pd-catalyzed annulation strategy. An asymmetric catalytic variant provides a rapid and efficient means to access these heterocycles with...

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Allen BD, Connolly MJ, Harrity JP. A Pd-Catalyzed Synthesis of Functionalized Piperidines. Chemistry. 2016;22(37):13000-3doi: 10.1002/chem.201602586.
Allen, B. D., Connolly, M. J., & Harrity, J. P. (2016). A Pd-Catalyzed Synthesis of Functionalized Piperidines. Chemistry (Weinheim an der Bergstrasse, Germany), 22(37), 13000-3. https://doi.org/10.1002/chem.201602586
Allen, Benjamin D W, et al. "A Pd-Catalyzed Synthesis of Functionalized Piperidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,37 (2016): 13000-3. doi: https://doi.org/10.1002/chem.201602586
Allen BD, Connolly MJ, Harrity JP. A Pd-Catalyzed Synthesis of Functionalized Piperidines. Chemistry. 2016 Sep 05;22(37):13000-3. doi: 10.1002/chem.201602586. Epub 2016 Jul 05. PMID: 27273202.
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Potent and Selective Amidopyrazole Inhibitors of IRAK4 That Are Efficacious in a Rodent Model of Inflammation.

ACS medicinal chemistry letters

McElroy WT, Tan Z, Ho G, Paliwal S, Li G, Seganish WM, Tulshian D, Tata J, Fischmann TO, Sondey C, Bian H, Bober L, Jackson J, Garlisi CG, Devito K, Fossetta J, Lundell D, Niu X.
PMID: 26101573
ACS Med Chem Lett. 2015 May 12;6(6):677-82. doi: 10.1021/acsmedchemlett.5b00106. eCollection 2015 Jun 11.

IRAK4 is a critical upstream kinase in the IL-1R/TLR signaling pathway. Inhibition of IRAK4 is hypothesized to be beneficial in the treatment of autoimmune related disorders. A screening campaign identified a pyrazole class of IRAK4 inhibitors that were determined...

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McElroy WT, Tan Z, Ho G, et al. Potent and Selective Amidopyrazole Inhibitors of IRAK4 That Are Efficacious in a Rodent Model of Inflammation. ACS Med Chem Lett. 2015;6(6):677-82doi: 10.1021/acsmedchemlett.5b00106.
McElroy, W. T., Tan, Z., Ho, G., Paliwal, S., Li, G., Seganish, W. M., Tulshian, D., Tata, J., Fischmann, T. O., Sondey, C., Bian, H., Bober, L., Jackson, J., Garlisi, C. G., Devito, K., Fossetta, J., Lundell, D., & Niu, X. (2015). Potent and Selective Amidopyrazole Inhibitors of IRAK4 That Are Efficacious in a Rodent Model of Inflammation. ACS medicinal chemistry letters, 6(6), 677-82. https://doi.org/10.1021/acsmedchemlett.5b00106
McElroy, William T, et al. "Potent and Selective Amidopyrazole Inhibitors of IRAK4 That Are Efficacious in a Rodent Model of Inflammation." ACS medicinal chemistry letters vol. 6,6 (2015): 677-82. doi: https://doi.org/10.1021/acsmedchemlett.5b00106
McElroy WT, Tan Z, Ho G, Paliwal S, Li G, Seganish WM, Tulshian D, Tata J, Fischmann TO, Sondey C, Bian H, Bober L, Jackson J, Garlisi CG, Devito K, Fossetta J, Lundell D, Niu X. Potent and Selective Amidopyrazole Inhibitors of IRAK4 That Are Efficacious in a Rodent Model of Inflammation. ACS Med Chem Lett. 2015 May 12;6(6):677-82. doi: 10.1021/acsmedchemlett.5b00106. eCollection 2015 Jun 11. PMID: 26101573; PMCID: PMC4468401.
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Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts.

Chemistry (Weinheim an der Bergstrasse, Germany)

Renom-Carrasco M, Gajewski P, Pignataro L, de Vries JG, Piarulli U, Gennari C, Lefort L.
PMID: 27140832
Chemistry. 2016 Jul 04;22(28):9528-32. doi: 10.1002/chem.201601501. Epub 2016 Jun 03.

The use of an equivalent amount of an organic base leads to high enantiomeric excess in the asymmetric hydrogenation of N-benzylated 3-substituted pyridinium salts into the corresponding piperidines. Indeed, in the presence of Et3 N, a Rh-JosiPhos catalyst reduced...

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Renom-Carrasco M, Gajewski P, Pignataro L, et al. Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry. 2016;22(28):9528-32doi: 10.1002/chem.201601501.
Renom-Carrasco, M., Gajewski, P., Pignataro, L., de Vries, J. G., Piarulli, U., Gennari, C., & Lefort, L. (2016). Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry (Weinheim an der Bergstrasse, Germany), 22(28), 9528-32. https://doi.org/10.1002/chem.201601501
Renom-Carrasco, Marc, et al. "Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,28 (2016): 9528-32. doi: https://doi.org/10.1002/chem.201601501
Renom-Carrasco M, Gajewski P, Pignataro L, de Vries JG, Piarulli U, Gennari C, Lefort L. Asymmetric Hydrogenation of 3-Substituted Pyridinium Salts. Chemistry. 2016 Jul 04;22(28):9528-32. doi: 10.1002/chem.201601501. Epub 2016 Jun 03. PMID: 27140832.
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Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes.

The Journal of organic chemistry

René O, Stepek IA, Gobbi A, Fauber BP, Gaines S.
PMID: 26378765
J Org Chem. 2015 Oct 16;80(20):10218-25. doi: 10.1021/acs.joc.5b01846. Epub 2015 Oct 01.

A palladium(0)-catalyzed rearrangement of piperidones and piperidines bearing a spirocyclopropane ring was developed. The ring expansion reaction led to a variety of functionalized caprolactam and azepane products in good to excellent yields. Experimental and computational mechanistic studies revealed an...

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René O, Stepek IA, Gobbi A, et al. Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes. J Org Chem. 2015;80(20):10218-25doi: 10.1021/acs.joc.5b01846.
René, O., Stepek, I. A., Gobbi, A., Fauber, B. P., & Gaines, S. (2015). Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes. The Journal of organic chemistry, 80(20), 10218-25. https://doi.org/10.1021/acs.joc.5b01846
René, Olivier, et al. "Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes." The Journal of organic chemistry vol. 80,20 (2015): 10218-25. doi: https://doi.org/10.1021/acs.joc.5b01846
René O, Stepek IA, Gobbi A, Fauber BP, Gaines S. Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes. J Org Chem. 2015 Oct 16;80(20):10218-25. doi: 10.1021/acs.joc.5b01846. Epub 2015 Oct 01. PMID: 26378765.
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Discovery of Novel 3,3-Disubstituted Piperidines as Orally Bioavailable, Potent, and Efficacious HDM2-p53 Inhibitors.

ACS medicinal chemistry letters

Bogen SL, Pan W, Gibeau CR, Lahue BR, Ma Y, Nair LG, Seigel E, Shipps GW, Tian Y, Wang Y, Lin Y, Liu M, Liu S, Mirza A, Wang X, Lipari P, Seidel-Dugan C, Hicklin DJ, Bishop WR, Rindgen D, Nomeir A, Prosise W, Reichert P, Scapin G, Strickland C, Doll RJ.
PMID: 26985323
ACS Med Chem Lett. 2016 Jan 20;7(3):324-9. doi: 10.1021/acsmedchemlett.5b00472. eCollection 2016 Mar 10.

A new subseries of substituted piperidines as p53-HDM2 inhibitors exemplified by 21 has been developed from the initial lead 1. Research focused on optimization of a crucial HDM2 Trp23-ligand interaction led to the identification of 2-(trifluoromethyl)thiophene as the preferred...

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Bogen SL, Pan W, Gibeau CR, et al. Discovery of Novel 3,3-Disubstituted Piperidines as Orally Bioavailable, Potent, and Efficacious HDM2-p53 Inhibitors. ACS Med Chem Lett. 2016;7(3):324-9doi: 10.1021/acsmedchemlett.5b00472.
Bogen, S. L., Pan, W., Gibeau, C. R., Lahue, B. R., Ma, Y., Nair, L. G., Seigel, E., Shipps, G. W., Tian, Y., Wang, Y., Lin, Y., Liu, M., Liu, S., Mirza, A., Wang, X., Lipari, P., Seidel-Dugan, C., Hicklin, D. J., Bishop, W. R., Rindgen, D., Nomeir, A., Prosise, W., Reichert, P., Scapin, G., Strickland, C., & Doll, R. J. (2016). Discovery of Novel 3,3-Disubstituted Piperidines as Orally Bioavailable, Potent, and Efficacious HDM2-p53 Inhibitors. ACS medicinal chemistry letters, 7(3), 324-9. https://doi.org/10.1021/acsmedchemlett.5b00472
Bogen, Stéphane L, et al. "Discovery of Novel 3,3-Disubstituted Piperidines as Orally Bioavailable, Potent, and Efficacious HDM2-p53 Inhibitors." ACS medicinal chemistry letters vol. 7,3 (2016): 324-9. doi: https://doi.org/10.1021/acsmedchemlett.5b00472
Bogen SL, Pan W, Gibeau CR, Lahue BR, Ma Y, Nair LG, Seigel E, Shipps GW, Tian Y, Wang Y, Lin Y, Liu M, Liu S, Mirza A, Wang X, Lipari P, Seidel-Dugan C, Hicklin DJ, Bishop WR, Rindgen D, Nomeir A, Prosise W, Reichert P, Scapin G, Strickland C, Doll RJ. Discovery of Novel 3,3-Disubstituted Piperidines as Orally Bioavailable, Potent, and Efficacious HDM2-p53 Inhibitors. ACS Med Chem Lett. 2016 Jan 20;7(3):324-9. doi: 10.1021/acsmedchemlett.5b00472. eCollection 2016 Mar 10. PMID: 26985323; PMCID: PMC4789661.
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Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations.

Organic letters

Wang Z, Xu H, Su Q, Hu P, Shao PL, He Y, Lu Y.
PMID: 28560873
Org Lett. 2017 Jun 16;19(12):3111-3114. doi: 10.1021/acs.orglett.7b01221. Epub 2017 May 31.

A phosphine-catalyzed novel enantioselective [4 + 2]-annulation reaction between allene ketones and 1-azadienes has been developed, and tetrahydropyridines were obtained in good yields and with excellent enantioselectivities. Subsequent exposure of tetrahydropyridines to benzyne leads to a [2 + 2]-cyclization,...

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Wang Z, Xu H, Su Q, et al. Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations. Org Lett. 2017;19(12):3111-3114doi: 10.1021/acs.orglett.7b01221.
Wang, Z., Xu, H., Su, Q., Hu, P., Shao, P. L., He, Y., & Lu, Y. (2017). Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations. Organic letters, 19(12), 3111-3114. https://doi.org/10.1021/acs.orglett.7b01221
Wang, Zhen, et al. "Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations." Organic letters vol. 19,12 (2017): 3111-3114. doi: https://doi.org/10.1021/acs.orglett.7b01221
Wang Z, Xu H, Su Q, Hu P, Shao PL, He Y, Lu Y. Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations. Org Lett. 2017 Jun 16;19(12):3111-3114. doi: 10.1021/acs.orglett.7b01221. Epub 2017 May 31. PMID: 28560873.
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Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Feraldi-Xypolia A, Gomez Pardo D, Cossy J.
PMID: 26218227
Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23.

A ring contraction of 3-hydroxy-3-(trifluoromethyl)piperidines was achieved via an aziridinium intermediate. This contraction facilitates the synthesis of a series of 2-substituted 2-(trifluoromethyl)pyrrolidines incorporating a quaternary center at the C2 position.

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Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015;21(37):12876-80doi: 10.1002/chem.201502084.
Feraldi-Xypolia, A., Gomez Pardo, D., & Cossy, J. (2015). Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry (Weinheim an der Bergstrasse, Germany), 21(37), 12876-80. https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia, Alexandra, et al. "Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,37 (2015): 12876-80. doi: https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23. PMID: 26218227.
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Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant.

Organic letters

Zhu H, Chen P, Liu G.
PMID: 25742490
Org Lett. 2015 Mar 20;17(6):1485-8. doi: 10.1021/acs.orglett.5b00373. Epub 2015 Mar 05.

A palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes was developed in which H2O2 was used as the sole oxidant. A variety of 3-acetoxylated piperidines were obtained in good yields with good to excellent regio- and diastereoselectivities. Mechanistic study revealed that...

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Zhu H, Chen P, Liu G. Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant. Org Lett. 2015;17(6):1485-8doi: 10.1021/acs.orglett.5b00373.
Zhu, H., Chen, P., & Liu, G. (2015). Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant. Organic letters, 17(6), 1485-8. https://doi.org/10.1021/acs.orglett.5b00373
Zhu, Haitao, et al. "Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant." Organic letters vol. 17,6 (2015): 1485-8. doi: https://doi.org/10.1021/acs.orglett.5b00373
Zhu H, Chen P, Liu G. Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant. Org Lett. 2015 Mar 20;17(6):1485-8. doi: 10.1021/acs.orglett.5b00373. Epub 2015 Mar 05. PMID: 25742490.
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Intramolecular radical rearrangement reactions of 2-methyleneaziridines: application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines.

Organic letters

Prévost N, Shipman M.
PMID: 11463322
Org Lett. 2001 Jul 26;3(15):2383-5. doi: 10.1021/ol016194k.

[reaction: see text] Intramolecular 5-exo cyclization of 3-(2-methyleneaziridin-1-yl)propyl radicals leads to the generation of a highly strained, bicyclic aziridinylcarbinyl radical that undergoes C-N bond fission to the ring-expanded aminyl radical. This methodology provides access to substituted 3-methylenepiperidines and, by...

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Prévost N, Shipman M. Intramolecular radical rearrangement reactions of 2-methyleneaziridines: application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines. Org Lett. 2001;3(15):2383-5doi: 10.1021/ol016194k.
Prévost, N., & Shipman, M. (2001). Intramolecular radical rearrangement reactions of 2-methyleneaziridines: application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines. Organic letters, 3(15), 2383-5. https://doi.org/10.1021/ol016194k
Prévost, N, and Shipman, M. "Intramolecular radical rearrangement reactions of 2-methyleneaziridines: application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines." Organic letters vol. 3,15 (2001): 2383-5. doi: https://doi.org/10.1021/ol016194k
Prévost N, Shipman M. Intramolecular radical rearrangement reactions of 2-methyleneaziridines: application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines. Org Lett. 2001 Jul 26;3(15):2383-5. doi: 10.1021/ol016194k. PMID: 11463322.
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