Synthesis of Unsymmetrical Dithioacetals: An Efficient Synthesis of a Novel LTD4 Antagonist, L-660,711

Abstract

An efficient four-step synthesis of the potent LTD4 antagonist L-660,711 (1) is described. The key step involves selective conversion of aldehyde 2 to the unsymmetrical dithioacetal 7, via O-trimethylsilyl hemithioacetal 10. This specific cleavage of the carbon-oxygen bond of a mixed 0,S-acetal permits the unprecedented synthesis of unsymmetrical dithioacetals. © 1989, American Chemical Society. All rights reserved.