Organic & biomolecular chemistry

Total synthesis and absolute configuration of malyngamide W

XL Qi, JT Zhang, JP Feng, XP Cao

Index: Qi, Xian-Liang; Zhang, Jun-Tao; Feng, Jian-Peng; Cao, Xiao-Ping Organic and Biomolecular Chemistry, 2011 , vol. 9, # 10 p. 3817 - 3824

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Citation Number: 11

Abstract

A concise enantioselective synthesis of malyngamide W (1) and its 2′-epimer was described. The strategy was based on three key steps:(1) ozonolysis of compound 11 which was derived from (R)-(−)-carvone 8, followed by copper-iron-catalyzed rearrangement to give the key cyclohex-2-enone intermediate 5,(2) Nozaki–Hiyama–Kishi coupling reaction between aldehyde 4 and iodide 14 to afford alcohol 3, and (3) asymmetric (R)-CBS ...

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