Total synthesis of indole and dihydroindole alkaloids. XII. Selective functionalization of various bisindoles. Efficient syntheses of leurosine and related bisindole alkaloid derivatives

Studies involving selective functionalization of the indole unit in a number of bisindole alkaloids and related synthetic derivatives are described. These investigations include such reagents as tert-butyl hydroperoxide, which provides an efficient procedure for epoxidation of olefinic linkages, mer...

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Published inCanadian journal of chemistry Vol. 56; no. 1; pp. 62 - 70
Main Authors Kutney, James P, Balsevich, John, Bokelman, Gordon H, Hibino, Toshihiko, Honda, Toshio, Itoh, Isamu, Ratcliffe, Arnold H, Worth, Brian R
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.01.1978
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Summary:Studies involving selective functionalization of the indole unit in a number of bisindole alkaloids and related synthetic derivatives are described. These investigations include such reagents as tert-butyl hydroperoxide, which provides an efficient procedure for epoxidation of olefinic linkages, mercuric acetate, osmium tetroxide, and iodine under basic conditions and oxygenation under acidic conditions. Efficient syntheses of leurosine ( 8 ) and various novel vinblastine derivatives are developed.
ISSN:0008-4042
1480-3291
DOI:10.1139/v78-011