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Synthesis of (-)-muricatacin.

Bioscience, biotechnology, and biochemistry (1993-06-01)
H Makabe, A Tanaka, T Oritani
ABSTRACT

The synthesis of (-)-muricatacin starting from 1-bromododecane and 2-pentyn-1-ol is described. 2-Pentadecyn-1-ol (4), which was prepared from 1-bromododecane (2) and 2-pentyn-1-ol (3), was converted to epoxy alcohol 6 through a two-step reaction sequence, 6 being successively submitted to tosylation, iodination, chain extension with tert-butyl lithioacetate, and acid-catalyzed cyclization to give (-)-muricatacin (1a). Recrystallization afforded optically pure 1a.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Pentyn-1-ol, 98%
Sigma-Aldrich
1-Bromododecane, purum, ≥95.0% (GC)