Total Synthesis of (+)‐Bourgeanic Acid Utilizing Desymmetrization Strategy
- 12 November 2010
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2011 (1) , 58-61
Abstract
A highly stereoselective total synthesis of an aliphatic depside (+)‐bourgeanic acid via (–)‐hemibourgeanic acid and bourgeanic lactone is described. The key steps involved in this synthesis are desymmetrization of bicyclic olefin with Brown's asymmetric hydroboration, Gillman's reaction, TEMPO‐BAIB mediated selective oxidation of 1,3‐diol, Yamaguchi macro‐lactonization and LiOH‐mediated partial hydrolysis of unusually stable eight‐membered cyclic dilactone.Keywords
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