Total synthesis of indole and dihydroindole alkaloids. II. Partial synthesis of some nine-membered ring intermediates from catharanthine

Journal of the American Chemical Society
1970.0

Abstract

An investigation of the reaction of catharanthine with zinc in glacial acetic acid is presented. Four isomeric carbomethoxydihydrocleavamine derivatives have been isolated and fully characterized. It is also shown that heating catharanthine in a mixture of acetic acid and sodium borohydride provides a very convenient method for the preparation of the previously unknown 18β-carbomethoxycleavamine. These compounds provide the desired intermediates for the synthesis of various Iboga alkaloids. © 1970, American Chemical Society. All rights reserved.

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