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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
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