Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

作者: Ruzhang Liu , Osvaldo Gutierrez , Dean J. Tantillo , Jeffrey Aubé

DOI: 10.1021/JA300369C

关键词: Enantioselective synthesisAllylic rearrangementStereoisomerismIntramolecular forceSchmidt reactionContext (language use)ChemistryPinnaic acidStereochemistryAzide

摘要: Pre-equilibration of an interconverting set isomeric allylic azides is coupled with intramolecular Schmidt reaction to afford substituted lactams stereoselectively. The effect substitution and a preliminary mechanistic study are reported. synthetic potential this method demonstrated in the context enantioselective synthesis advanced intermediate leading toward pinnaic acid.

参考文章(43)
Dominique Depré, Lian-Yong Chen, Léon Ghosez, A short multigram asymmetric synthesis of prostanoid scaffolds Tetrahedron. ,vol. 59, pp. 6797- 6812 ,(2003) , 10.1016/S0040-4020(03)00920-7
Derrick L. J. Clive, Maolin Yu, Jian Wang, Vince S. C. Yeh, Shunzhen Kang, Synthetic chemistry of halichlorine and the pinnaic acids Chemical Reviews. ,vol. 105, pp. 4483- 4514 ,(2005) , 10.1021/CR0406209
Angelica M. Meyer, Christopher E. Katz, Sze-Wan Li, David Vander Velde, Jeffrey Aubé, A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C. Organic Letters. ,vol. 12, pp. 1244- 1247 ,(2010) , 10.1021/OL100113R
N. Deborah Hewlett, Jeffrey Aubé, Jennifer L. Radkiewicz-Poutsma, Ab Initio Approach to Understanding the Stereoselectivity of Reactions between Hydroxyalkyl Azides and Ketones Journal of Organic Chemistry. ,vol. 69, pp. 3439- 3446 ,(2004) , 10.1021/JO035632T
H. S. Christie, C. H. Heathcock, Total synthesis of (+/-)-halichlorine, (+/-)-pinnaic acid, and (+/-)-tauropinnaic acid. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 101, pp. 12079- 12084 ,(2004) , 10.1073/PNAS.0403887101
Emmanuel Roulland, Angèle Chiaroni, Henri-Philippe Husson, A diastereoselective approach for an asymmetric synthesis in pinnaic acid series Tetrahedron Letters. ,vol. 46, pp. 4065- 4068 ,(2005) , 10.1016/J.TETLET.2005.04.019
Hong-Lu Zhang, Gang Zhao, Yu Ding, Bin Wu, An Efficient and Enantioselective Approach to the Azaspirocyclic Core of Alkaloids:  Formal Synthesis of Halichlorine and Pinnaic Acid The Journal of Organic Chemistry. ,vol. 70, pp. 4954- 4961 ,(2005) , 10.1021/JO047882V
C. Houge, A. M. Frisque-Hesbain, A. Mockel, L. Ghosez, J. P. Declercq, G. Germain, M. Van Meerssche, Models for Asymmetric [2+2] Cyclo-additions Journal of the American Chemical Society. ,vol. 104, pp. 2920- 2921 ,(1982) , 10.1021/JA00374A036
Shu Xu, Hirokazu Arimoto, Daisuke Uemura, Asymmetric Total Synthesis of Pinnaic Acid Angewandte Chemie. ,vol. 46, pp. 5746- 5749 ,(2007) , 10.1002/ANIE.200701581
Aaron Wrobleski, Kiran Sahasrabudhe, Jeffrey Aubé, Asymmetric total synthesis of dendrobatid alkaloid 251F. Journal of the American Chemical Society. ,vol. 124, pp. 9974- 9975 ,(2002) , 10.1021/JA027113Y