Total Synthesis of Lemaireocereine

Hisashi ISHII; Tsutomu ISHIKAWA; Shuji OHTA; Masahiro SUZUKI; Takashi HARAYAMA

doi:10.1248/cpb.40.1993

Hisashi ISHII, Tsutomu ISHIKAWA, Shuji OHTA, Masahiro SUZUKI, Takashi HARAYAMA

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Keywords: lemaireocereine, successive substitution, bensofuran ring fission, synthesis, hydrogenolysis, simple isoquinoline, Boc, Cbz

JOURNAL FREE ACCESS

1992 Volume 40 Issue 8 Pages 1993-1996

DOI https://doi.org/10.1248/cpb.40.1993

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Abstract

By utilizing newly developed synthetic methods i.e. 2-methylbenzofuran formation by CsF-mediated Claisen rearrangement of an aryl propargyl ether and its transformation to a salicylaldehyde by oxidative cleavage of the furan ring, total synthesis of a coctus alkaloid, lemaireocereine (2), was accomplished via ten steps from the aldehyde (4) in 22% yield.

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