A novel synthesis of (2S)-4-oxo-pipecofic acid is reported. The synthetic route employs as a key step the diastereoselective cycloaddition of the N-glycosylnitrone ? to methylenecyclopropane followed by thermal rearrangement of the spirocyclopropaneisoxazolidine 8a. Stereoselective reduction of the N-BOC methyl ester of 4-oxopipecolic acid by L-selectride ® gives the protected cis- 4-hydroxy-pipecolic acid 14
A New Synthesis of (2S)-4-Oxopipecolic Acid by Thermal Rearrangement ofEnantiopure Spirocyclopropaneisoxazolidine / F. Machetti; F. M. Cordero; F. De Sarlo; A. Guarna; A. Brandi. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 37:(1996), pp. 4205-4208.
A New Synthesis of (2S)-4-Oxopipecolic Acid by Thermal Rearrangement ofEnantiopure Spirocyclopropaneisoxazolidine
MACHETTI, FABRIZIO;CORDERO, FRANCA MARIA;DE SARLO, FRANCESCO;GUARNA, ANTONIO;BRANDI, ALBERTO
1996
Abstract
A novel synthesis of (2S)-4-oxo-pipecofic acid is reported. The synthetic route employs as a key step the diastereoselective cycloaddition of the N-glycosylnitrone ? to methylenecyclopropane followed by thermal rearrangement of the spirocyclopropaneisoxazolidine 8a. Stereoselective reduction of the N-BOC methyl ester of 4-oxopipecolic acid by L-selectride ® gives the protected cis- 4-hydroxy-pipecolic acid 14
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