Total synthesis of (+)-roxaticin via C− C bond forming transfer hydrogenation: a departure from stoichiometric chiral reagents, auxiliaries, and premetalated …

…, A Hassan, IS Kim, MJ Krische

Index: Han, Soo Bong; Hassan, Abbas; Kim, In Su; Krische, Michael J. Journal of the American Chemical Society, 2010 , vol. 132, # 44 p. 15559 - 15561

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Citation Number: 67

Abstract

A total synthesis of the oxo-polyene macrolide (+)-roxaticin is achieved in 20 steps from 1, 3- propanediol. In this approach, 9 of 10 C− C bonds formed in the longest linear sequence are made via metal catalysis, including 7 C− C bonds formed by iridium catalyzed alcohol C− C coupling. Notably, the present synthesis, which represents the most concise preparation of any oxo-polyene macrolide reported to date, is achieved in the absence of chiral reagents ...