From Central to Axial to Central Chirality: Enantioselective Construction of the trans-4,5,9,10-Tetrahydroxy-9,10-dihydrophenanthrene System

✍ Scribed by Georgi Stavrakov; Manfred Keller; Bernhard Breit

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 278 KB
• Volume: 2007
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200700583

✦ Synopsis

Abstract

Enantioselective synthesis of the core trans‐4,5,9,10‐tetrahydroxy‐9,10‐dihydrophenanthrene parent system of the antibiotics benanimicin, pradimicin and FD 594 has been accomplished. The synthesis employs a chiral tether approach and makes use of efficient central to axial to central chirality transfer. Key to success was an “imine‐directed” atropdiastereoselective Ullmann coupling under mild reaction conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)