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

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

doi:10.1016/0957-4166(96)00038-9

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

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-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 language	English
Pages (from-to)	537-558
Journal	Tetrahedron Asymmetry
Volume	7
Issue number	2
DOIs	https://doi.org/10.1016/0957-4166(96)00038-9
Publication status	Published - 1 Jan 1996

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title = "Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs",

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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AU - Jiménez, José M.

AU - Rifé, Joan

AU - Ortuño, Rosa M.

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N2 - 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.

AB - 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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DO - 10.1016/0957-4166(96)00038-9

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