Synthesis of (+)-Vinblastine and Its Analogues
- 13 October 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (23) , 4737-4740
- https://doi.org/10.1021/ol702040y
Abstract
A synthetic route to vinblastine and its analogues with an ethynyl group, which features a stereoselective coupling of an 11-membered key intermediate with vindoline, is described. Transformations of the alkynyl moiety including a partial reduction as well as a Sonogashira coupling furnished a variety of analogues.Keywords
This publication has 19 references indexed in Scilit:
- Structural basis for the regulation of tubulin by vinblastineNature, 2005
- Ns strategies: a highly versatile synthetic method for aminesChemical Communications, 2003
- Stereocontrolled Total Synthesis of (+)-VinblastineJournal of the American Chemical Society, 2002
- Radical Cyclization of 2-Alkenylthioanilides: A Novel Synthesis of 2,3-Disubstituted IndolesJournal of the American Chemical Society, 1999
- Nonoxidative coupling methodology for the synthesis of the antitumor bisindole alkaloid vinblastine and a lower-half analog: solvent effect on the stereochemistry of the crucial C-15/C-18' bondJournal of the American Chemical Society, 1992
- Enantioselective syntheses of vinblastine, leurosidine, vincovaline and 20'-epi-vincovalineThe Journal of Organic Chemistry, 1991
- A Highly Efficient and Commercially Important Synthesis of the Antitumor Catharanthus Alkaloids Vinblastine and Leurosidine from Catharanthine and VindolineHETEROCYCLES, 1988
- Preparation of vinblastine, vincristine, and leurosidine, antitumor alkaloids from Catharanthus species (Apocynaceae)Journal of the American Chemical Society, 1979
- Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don.) V.**Organic Chemical Development and Lilly Research Laboratories, Eli Lilly and Co., Indianapolis, Ind.Journal of the American Pharmaceutical Association (Scientific ed.), 1959
- ROLE OF CHANCE OBSERVATIONS IN CHEMOTHERAPY: VINCA ROSEA*Annals of the New York Academy of Sciences, 1958