Enantioselective total synthesis of (-)-chlorothricolide via the tandem inter-and intramolecular Diels-Alder reaction of a hexaenoate intermediate

WR Roush, RJ Sciotti

Index: Roush, William R.; Sciotti, Richard J. Journal of the American Chemical Society, 1998 , vol. 120, # 30 p. 7411 - 7419

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Citation Number: 108

Abstract

An enantioselective total synthesis of (-)-chlorothricolide (1) has been completed via a route involving the tandem inter-and intramolecular Diels-Alder (IMDA) reaction of hexaenoate 19 and the chiral dienophile (R)-12. This reaction, which establishes seven asymmetric centers in a single operation, is feasible only by virtue of the high diastereofacial and exo selectivity of dienophile 12. The C (9)-trimethylsilyl steric directing group of 19 also plays a key role ...