Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Zhurakovskyi, Oleksandr; TÜRKMEN, YUNUS; Loeffler, Lorenz; Moorthie, Vijayalakshmi; Chen, C.; Shaw, Michael; Crimmin, Mark; Ferrara, Marco; Ahmad, Mushtaq; Ostovar, Mehrnoosh; Matlock, Johnathan; Aggarwal, Varinder

doi:10.1002/anie.201712065

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Zhurakovskyi O., TÜRKMEN Y. E., Loeffler L. E., Moorthie V. A., Chen C. C., Shaw M. A., ...Daha Fazla

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, cilt.57, sa.5, ss.1346-1350, 2018 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 57 Sayı: 5
Basım Tarihi: 2018
Doi Numarası: 10.1002/anie.201712065
Dergi Adı: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
Sayfa Sayıları: ss.1346-1350
Orta Doğu Teknik Üniversitesi Adresli: Hayır

Özet

A convergent, nine-step (LLS), enantioselective synthesis of -cyclopiazonic acid and related natural products is reported. The route features a)an enantioselective aziridination of an imine with a chiral sulfur ylide; b)a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c)installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N-O cleavage of a bromoisoxazole.