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Highly diastereoselective synthesis and template manipulation of the thiazolo[2,3-a]isoindolin-1-one ring system

✍ Scribed by Steven M Allin; Darshan G Vaidya; Michael I Page; Alexandra M.Z Slawin; Tim Smith

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
130 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Condensation of 2-acetyl benzoic acid with L-cysteine esters proceeds with extremely high diastereoselectivity to produce the desired thiazolo[2,3-a]isoindolin-1-one products in good yield. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystallography. Stereoselective enolate alkylation of this substrate has been investigated as a method to manipulate the ring skeleton, and was found to proceed with up to exclusive levels of stereoselectivity.

πŸ“œ SIMILAR VOLUMES

A Highly Stereoselective Synthesis of th
A Highly Stereoselective Synthesis of the Indolo[2,3-a]quinolizine Ring System and Application to Natural Product Synthesis
✍ Steven M. Allin; Christopher I. Thomas; James E. Allard; Kevin Doyle; Mark R. J. πŸ“‚ Article πŸ“… 2005 πŸ› John Wiley and Sons 🌐 English βš– 162 KB

## Abstract We present a facile and highly stereoselective approach to the indolo[2,3‐__a__]quinolizine ring system from a readily available, non‐racemic chiral template. We demonstrate the potential for application of this methodology to natural product synthesis through conversion of the template