Synthesis of enantiopure isoprene epoxides from (S)-lactic acid via 'dispoke'intermediates

…, C Bleasdale, BT Golding, WP Watson

Index: Zhang, Daping; Bleasdale, Christine; Golding, Bernard T.; Watson, William P. Chemical Communications, 2000 , # 13 p. 1141 - 1142

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Citation Number: 9

Abstract

The mechanistic toxicology of isoprene is a subject of considerable current importance. 1 In this context, samples of single enantiomers of isoprene epoxides are required for the preparation of reference standards of DNA adducts. We describe efficient syntheses of enantiomerically pure (S)-2-ethenyl-2-methyloxirane 1 and (2R,2′S)-2-methylbioxirane 2, using as starting material the 'dispoke protected lactate' 3 derived from (S)-lactic acid. 2 An eight-step synthesis of ...