Total synthesis of indole and dihydroindole alkaloids. XI.1,2 The synthesis of leurosine and the coupling of 3α,4α-substituted catharanthine derivatives with vindoline
- 15 September 1977
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 55 (18) , 3235-3242
- https://doi.org/10.1139/v77-450
Abstract
A detailed study involving the Polonovski-type coupling of vindoline (2) with several novel catharanthine derivatives is described. Coupling of vindoline (2) with the N-oxide intermediate of 3β,4β-epoxydihydrocatharanthine (1) provides a laboratory synthesis of the bisindole alkaloid leurosine (3, R=CO2CH3) and an unambiguous proof of the stereochemistry of the epoxide function in that alkaloid. The coupling of 2 with the N-oxides of 3α,4α-epoxydihydrocatharanthine (4) and 4α-hydroxydihydrocatharanthinic acid lactone (6) provide the rearranged bisindole products 5, 7, and 8.Keywords
This publication has 3 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. 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