Total synthesis of indole and dihydroindole alkaloids. XII. Selective functionalization of various bisindoles. Efficient syntheses of leurosine and related bisindole alkaloid derivatives
- 1 January 1978
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 56 (1), 62-70
- https://doi.org/10.1139/v78-011
Abstract
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.This publication has 4 references indexed in Scilit:
- Total synthesis of indole and dihydroindole alkaloids. XI.1,2 The synthesis of leurosine and the coupling of 3α,4α-substituted catharanthine derivatives with vindolineCanadian Journal of Chemistry, 1977
- Total synthesis of indole and dihydroindole alkaloids. X.1,2 The preparation of novel oxygenated catharanthine derivativesCanadian Journal of Chemistry, 1977
- Total Synthesis of Indole and Dihydroindole Alkaloids. IX Studies on the synthesis of bisindole alkaloids in the vinblastine‐ vincristine series. The biogenetic approachHelvetica Chimica Acta, 1976
- Application of a modification of the Polonovski reaction to the synthesis of vinblastine-type alkaloidsJournal of the American Chemical Society, 1976