Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

José M. Jiménez, Joan Rifé, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review

69 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)537-558
JournalTetrahedron Asymmetry
Volume7
Issue number2
DOIs
Publication statusPublished - 1 Jan 1996

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