Total synthesis of (+)-crocacin C

Chakraborty, Tushar K. ; Jayaprakash, Sarva ; Laxman, Pasunoori (2001) Total synthesis of (+)-crocacin C Tetrahedron, 57 (46). pp. 9461-9467. ISSN 0040-4020

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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 auxiliary, lithium dimethylcuprate opening of a C6-C7 chiral epoxide prepared by Sharpless epoxidation method established the remaining two stereocentres.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Antifungals; Cytotoxins; Aldol Reactions; Katsuki-sharpless Reactions
ID Code:20582
Deposited On:20 Nov 2010 14:16
Last Modified:22 May 2011 15:47

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