Bioscience, Biotechnology, and Biochemistry 2003-03-01

Total synthesis of 0231B, an inhibitor of 3alpha-hydroxysteroid dehydrogenase produced by Streptomyces sp. HKI0231.

Taichi Komoda, Yoshihiko Shinoda, Shin-ichi Nakatsuka

Index: Biosci. Biotechnol. Biochem. 67(3) , 659-62, (2003)

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Abstract

The new inhibitors of 3alpha-hydroxysteroid dehydrogenase, 0231A 1 and 0231B 2, have a unique benz[c,d]indol-3(1H)-one structure in their molecules. In our advanced studies on indole chemistry, we have developed an efficient synthetic method for benz[c,d]indol-3(1H)-one derivatives. We report here its application to the synthesis of 0231B in 10 steps (8.1% overall yield) from 6-methylindole 8 by introducing an acyl group into the 3-position of the indole nucleus, cyclization of the side chain at the 3-position to the 4-position and subsequent elimination of the phenyl group, and conjugate addition of the substituted phenyl group.