Abstract

Abstract The syntheses of (−)-allo-coronamic acid, (−)-allo-norcoronamic acid, (−)-(Z)-2,3-methanohomoserine, (−)-(Z)-2,3-methanomethionine, and (2S,3R)-Cbz-cyclo-Asp-OMe have been achieved in 45–68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in turn, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in side-chain functionalization to the respective target molecules are discussed.

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