Modification of α-Santonin. I. An Abnormal Chlorination of 3-Hydroxy-4, 5-epoxy-6, 11βH-eudesm-1-en-6, 12-olide with Methanesulfonyl Chloride

Abstract

An abnormal, stereospecific chlorination of 3-hydroxy-4, 5-epoxy-6, 11βH-eudesm-1-en-6, 12-olide (5, 6, 7 and 8) with methanesulfonyl chloride (or p-toluenesulfonyl chloride)-pyridine is described. The stereochemistry of the chlorides (9, 10, 11 and 12) were confirmed by their nuclear magnetic resonance spectra and chemical reactions.