The Total Synthesis of A-23187 and Related Enantioselective Aldol Condensations

Author: Taber, Terry Ray

Year: 1981

Degree: Dissertation (Ph.D.)

Advisor: Dervan, Peter B.

Committee Members: Dervan, Peter B.; Evans, David A.; Richards, John H.; Dougherty, Dennis A.

Option: Chemistry

DOI: 10.7907/xcz4-1016

Abstract

A-23187 is a calcium specific ionophore which was isolated from Streptomyces chartreusis. The total synthesis of A-23187 and synthesis of related diacid ionophores are discussed.

[Chemical structure included in scanned thesis' Abstract, p. v.]

The synthetic approach used for A-23187 required stereoselective aldol condensations. In this regard, the development of enantioselective aldol condensations with boron enolates is detailed. The general applications of such condensations are also discussed.

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