Synthesis of Vinca alkaloids and related compounds. 21. Preparation of (.+-.)-eburnamonine, (.+-.)-3-epieburnamonine, and (.+-.)-C-norquebrachamine from a common intermediate

The pentacyclic indole derivatives (.+-.)-eburnamonine (8b) and (.+-.)-3-epieburnamonine (17b) and the tetracyclic (.+-.)-C-norquebrachamine (10) have been synthesized from the easily available common intermediate 2a. In the course of the syntheses some unexpected transformations were observed. Stru...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 50; no. 20; pp. 3760 - 3767
Main Authors Kalaus, Gyoergy, Malkieh, Numan, Katona, Ildiko, Kajtar-Peredy, Maria, Koritsanszky, Tibor, Kalman, Alajos, Szabo, Lajos, Szantay, Csaba
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.10.1985
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet full text

Cover

More Information
Summary:The pentacyclic indole derivatives (.+-.)-eburnamonine (8b) and (.+-.)-3-epieburnamonine (17b) and the tetracyclic (.+-.)-C-norquebrachamine (10) have been synthesized from the easily available common intermediate 2a. In the course of the syntheses some unexpected transformations were observed. Structure elucidations of new products were performed partly by X-ray analysis.
Bibliography:ark:/67375/TPS-X52TM5NK-G
istex:BE8E6819246F979E07048816C28D54A5021DDCF5
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00220a017