C-1 Reactivity of 2, 3-epoxy alcohols via oxirane opening with metal halides: applications and synthesis of naturally occurring 2, 3-octanediol, muricatacin, 3-octanol, …

C Bonini, C Federici, L Rossi…

Index: Bonini, Carlo; Federici, Chiara; Rossi, Leucio; Righi, Giuliana Journal of Organic Chemistry, 1995 , vol. 60, # 15 p. 4803 - 4812

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Citation Number: 60

Abstract

The C-1 reactivity of 2, 3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2, 3-epoxy alcohols with LiI leads to 1-iodo 2, 3-diols with erythro or threo stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been ...