Stereoselective Aldol Condensations via Boron Enolates. The Syntheses of (+)-Prelog-Djerassi Lactone and (+)-Tylonolide

Author: Bartroli, Javier Francisco

Year: 1984

Degree: Dissertation (Ph.D.)

Advisor: Dougherty, Dennis A.

Committee Members: Evans, David A.; Collins, Terrence J.; Dervan, Peter B.; Dougherty, Dennis A.

Option: Chemistry

DOI: 10.7907/3v27-xh37

Abstract

The use of boron enolates of chiral N-acyl oxazolidinones i and ii in highly stereoselective aldol condensations is described. Mild base hydrolysis of the products affords optically pure erythro β-hydroxy acids and the chiral auxiliary, which can be reconverted into i or ii in one step.

The utility and scope of these reactions is demonstrated by the total syntheses of (+)-Prelog-Djerassi lactone and (+)-Tylonolide, cyclic 5,20-hemiacetal .

[Chemical structures included in scanned thesis' abstract, p. v.]

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