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A Unified Strategy for the Asymmetric Total Syntheses of Diversonol and Lachnone C

✍ Scribed by Dipl.-Chem. Manuel C. Bröhmer; Dr. Emmanuel Bourcet; Dr. Martin Nieger; Prof. Dr. Stefan Bräse

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
320 KB
Volume
17
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

A unified synthetic strategy for the asymmetric syntheses of the natural products diversonol and lachnone C was developed by using the domino vinylogous aldol–oxa‐Michael reaction as the enantioselective key step. Further transformations include dihydroxylation, lactol‐opening by a Wittig‐reaction, and lactonization. The obtained chromone lactones, a class of mycotoxins, can further be converted to tetrahydroxanthones by a Dieckmann condensation. This general method allows for the first time the enantioselective access to these classes of natural products and should be applicable to other members of the tetrahydroxanthone and chromone lactone families.

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