A versatile protocol for β-hydroxy-α-amino acids: an application to (4R)-4-[(e)-2-butenyl]-4n-dimethyl-l-threonine (MeBmt)

Rama Rao, A. V. ; Murali Dhar, T. G. ; Bose, D. Subhas ; Chakraborty, T. K. ; Gurjar, M. K. (1989) A versatile protocol for β-hydroxy-α-amino acids: an application to (4R)-4-[(e)-2-butenyl]-4n-dimethyl-l-threonine (MeBmt) Tetrahedron, 45 (23). pp. 7361-7370. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)89197-3

Abstract

cis -Oxazolidinone derivative (30) readily realised from chiral 2,3-epoxy alcohol (27) had been exploited in the synthesis of (4R̲)-4-[(E)-2-butenyl]-4,N-dimethyl-L-threonine (2), an unusual β-hydroxy-α-amino acid present in cyclosporin. The intrinsic feature of this approach involved facile isomerisation of cis-oxazolidinone derivative (31) into the trans -isomer (32) whose hydrolysis provided syn -β-hydroxy-α-amino acid.

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