Stereospecific synthesis of N-protected statine and its analogues via chiral tetramic acid
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1177-1182
- https://doi.org/10.1039/p19870001177
Abstract
The condensation of a chiral N-protected amino acid with Meldrum's acid in the presence of isopropenyl chloroformate (IPCF) and of 4-N,N-dimethylaminopyridine (DMAP) has been examined. The cyclisation of the reaction product, by heating in an organic solvent, gave the N-protected tetramic acid derivatives (4a–i) which, after reduction, afforded the corresponding threo-4-hydroxypyrrolidin-2- ones (5a–i). The regioselective alkaline or acid hydrolysis of the N-protected pyrrolidin-2-ones led to enantiomeric pure N- Boc-statine (6a) and its analogues (6b–i) in 40–60% yield from the N-protected amino acids. The corresponding statine methyl esters (7a–i) could also be synthesized in high yield.This publication has 7 references indexed in Scilit:
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