Highly Functionalised Pyroglutamates by Intramolecular Aldol Reactions: Towards the Pyroglutamate Skeleton of Oxazolomycin
- 1 July 1996
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1996 (07) , 612-614
- https://doi.org/10.1055/s-1996-5555
Abstract
Intramolecular aldol reactions of cis-N-acyloxazolidines 6a,b gave protected α-substituted pyroglutamates. The observed stereocontrol arises as a result of the chiral memory of the oxazolidine template, and regioselective enolate formation prior to ring closure. The major products, 10 and 12, have the correct relative stereochemistry for the oxazolomycin group of antitumour antibiotics.Keywords
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