Tetrahedron

Total synthesis of (+)-crocacin C

TK Chakraborty, S Jayaprakash, P Laxman

Index: Chakraborty, Tushar K; Jayaprakash, Sarva; Laxman, Pasunoori Tetrahedron, 2001 , vol. 57, # 46 p. 9461 - 9467

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Citation Number: 55

Abstract

The total synthesis of potent antifungal and cytotoxic agent (+)-crocacin C in optically pure form following a convergent strategy is described here in detail. The synthesis also established the absolute stereochemistry of the molecule having a (6S, 7S, 8R, 9S) configuration. While C8 and C9 stereocenters were built following a Ti (IV)-mediated diastereoselective 'non-Evans' aldol reaction based on 2-oxazolidinethione chiral ...