Synthesis and Facile One-pot Aldol/Elimination/Diels-Alder Reaction of ß-Keto-Z-Dienylamides as Cytochalasin C Intermediates1
- 1 September 1986
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 16 (11) , 1315-1333
- https://doi.org/10.1080/00397918608056379
Abstract
The coupling of chiral dienylamine 1ZE with ß-ketoesters and subsequent one-pot aldol reaction with derivatives of glyoxylic acid, acetylation of the hydroxyester thus produced, and intramolecular Diels-Alder reaction of the diene portion of the molecule with the incipient dienophile is described. The entire sequence generates all of the requisite chiral centers in the isoindolone skeleton of cytochalasin C simultaneously, in an overall yield of approximately 85%.Keywords
This publication has 3 references indexed in Scilit:
- Unusually facile aminolysis of β-ketoestersJournal of the Chemical Society, Chemical Communications, 1985
- Chiral and stereochemical control via intramolecular Diels-Alder reaction of Z dienesJournal of the American Chemical Society, 1982
- Cytochalasin support studies. 5. Conjugate addition of .beta.-oxo ester dianions to vinyl sulfones: a new procedure for seven-ring annulation. Synthesis of a chiral cytochalasin C intermediate via an intramolecular Diels-Alder reaction of a chiral Z dieneJournal of the American Chemical Society, 1982