Enantioselective Total Synthesis of cis-Trikentrin B

Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels−Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels−Alder adducts 9...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 1996-05, Vol.61 (10), p.3406-3416
Main Authors: Lee, Mase, Ikeda, Izumi, Kawabe, Tsuyoshi, Mori, Sayaka, Kanematsu, Ken
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels−Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels−Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels−Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo951767q