Synthesis of (-)-muricatacin.

Article abstract of DOI:10.1271/bbb.57.1028

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.

Full text of DOI:10.1271/bbb.57.1028

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Bioscience, Biotechnology, and Biochemistry
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Synthesis of (–)-Muricatacin
Hidefumi Makabea, Akira Tanakaa & Takayuki Oritania
a Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University,
1–1, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981,Japan
Published online: 12 Jun 2014.
To cite this article: Hidefumi Makabe, Akira Tanaka & Takayuki Oritani (1993) Synthesis of (–)-Muricatacin, Bioscience,
Biotechnology, and Biochemistry, 57:6, 1028-1029, DOI: 10.1271/bbb.57.1028
To link to this article: http://dx.doi.org/10.1271/bbb.57.1028
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