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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 20637 |
| Deposited On: | 20 Nov 2010 13:49 |
| Last Modified: | 20 May 2011 11:38 |
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