SYNTHESIS OF OPTICALLY ACTIVE TELEOCIDINS B-3 AND B-4

Kazuaki OKABE; Hideaki MURATAKE; Mitsutaka NATSUME

doi:10.1248/cpb.37.563

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

SYNTHESIS OF OPTICALLY ACTIVE TELEOCIDINS B-3 AND B-4

Kazuaki OKABE, Hideaki MURATAKE, Mitsutaka NATSUME

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Keywords: teleocidin B-3, teleocidin B-4, tumor promoter, total synthesis, BF₃·Et₂ O-catalyzed reaction, intramolecular Friedel-Crafts reaction

JOURNAL FREE ACCESS

1989 Volume 37 Issue 2 Pages 563-564

DOI https://doi.org/10.1248/cpb.37.563

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Abstract

The potent tumor promoters, optically active teleocidins B-3 (3) and B-4 (4), were totally synthesized mostly using our synthetic pathway for the teleocidin A series. The key reaction, the BF₃·Et₂ O-catalyzed intramolecular Friedel-Crafts cyclization, was applied at the final stage of the synthesis to the acetates (18a and 18b) to form the teleocidin B framework.

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