Bioorganic chemistry

Total synthesis of 12, 13-desoxyepothilone B (Epothilone D)

RL Broadrup, HM Sundar, CS Swindell

Index: Broadrup, Robert L.; Sundar, Hema M.; Swindell, Charles S. Bioorganic Chemistry, 2005 , vol. 33, # 2 p. 116 - 133

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Citation Number: 17

Abstract

A highly convergent total synthesis of 12, 13-desoxyepothilone B (4, Epothilone D) is described involving the coupling of vinyl iodide (5) and olefin (6). Key steps in the synthesis are the introduction of chirality at C15 via highly enantioselective lipase-mediated enzymatic resolution, diastereoselective alkylation at C8, highly diastereoselective Evans aldol reaction to establish C6–C7, and Mukaiyama aldol reaction to introduce chiral center C3. ...

~95%

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