Synthesis of unsymmetrical dithioacetals: an efficient synthesis of a novel LTD4 antagonist, L-660,711

JM McNamara, JL Leazer, M Bhupathy…

Index: McNamara, J. M.; Leazer, J. L.; Bhupathy, M.; Amato, J. S.; Reamer, R. A.; et al. Journal of Organic Chemistry, 1989 , vol. 54, # 15 p. 3718 - 3721

Full Text: HTML

Citation Number: 34

Abstract

An efficient four-step synthesis of the potent LTDl antagonist L-660,711 (1) is described. The key step involves selective conversion of aldehyde 2 to the unsymmetrical dithioacetal7, via 0-trimethylsilyl hemithioacetal 10. This specific cleavage of the carbon-oxygen bond of a mixed 0, s-acetal permits the unprecedented synthesis of unsymmetrical dithioacetals.