Stereoselective formal synthesis of aspergillide A |
| |
Authors: | Gowravaram Sabitha D. Vasudeva Reddy A. Senkara Rao J.S. Yadav |
| |
Affiliation: | Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 607, India |
| |
Abstract: | The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI2-induced intramolecular reductive cyclization as well as by using sequential α-aminooxylation, Horner-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen’s hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. |
| |
Keywords: | 14-Membered macrolide Z-Isomer Cross-metathesis RCM SmI2 α-Aminooxylation Oxa-Michael |
本文献已被 ScienceDirect 等数据库收录! |
|