Cyclofunctionalisation of epoxyalcohol derivatives. 4. Cyclisation of sulfonylacetate dianions: A synthesis of 'MeBMT'.

Article abstract of DOI:10.1016/S0040-4039(01)93415-X

α,α-Dianions, derived from arenesulfonylacetate esters of 2,3-epoxyalcohols, cyclised to give 3-arenesulfonyl-4-(1-hydroxyalkyl)-γ-butyrolactones. Dianion fragmentation to regenerate the epoxyalcohol was a competing, substrate-dependent process. Sulfonylactone (9) was elaborated efficiently to an advanced intermediate for the unusual aminoacid 'MeBMT' (5), and also to stereodefined cyclopropane derivatives.