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J Am Chem Soc. 2005 May 25;127(20):7290-1.

Total synthesis of mycalamide A.

Author information

1
Department of Chemistry, The University of Chicago, Illinois 60637, USA.

Abstract

This communication describes a concise and efficient total synthesis of mycalamide A by the convergent coupling of pederic acid unit with the mycalamine unit. The left-half, (+)-7-benzoylpederic acid, was synthesized from (2R,3R)-3-methylpent-4-en-2-ol in seven steps and 34.6% overall yield through a route that features a one-step Pd(II)-catalyzed tandem Wacker/Heck cyclization reaction to prepare the tetrahydropyran ring system. The right-half, the mycalamine unit, was synthesized in 21 steps and 10.5% overall yield from diethyl d-tartrate. Effective, stereoselective methods were developed for the assembly of the two parts to yield either mycalamide A or C(10)-epi-mycalamide A.

PMID:
15898759
DOI:
10.1021/ja050728l
[Indexed for MEDLINE]

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