First Desymmetrization of a Centrosymmetric Molecule in Natural Product Synthesis: Preparation of a Key Fragment in the Synthesis of Hemibrevetoxin B

✍ Scribed by Joanne M. Holland; Mark Lewis; Adam Nelson

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 88 KB
• Volume: 40
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3773(20011105)40:21<4082::aid-anie4082>3.0.co;2-t

✦ Synopsis

Exploitation of molecular symmetry can greatly improve the efficiency of syntheses. The symmetry embedded in the centrosymmetric AB dioxepane fragment of hemibrevetoxin B was exploited for the first time in the preparation of an established intermediate in its total synthesis. Desymmetrization of the centrosymmetric diepoxide 1 by enantioselective epoxide hydrolysis followed by acetonization gave the known synthetic intermediate 2.