Total synthesis of (+)-crocacin D

Chakraborty, Tushar K. ; Laxman, Pasunoori (2002) Total synthesis of (+)-crocacin D Tetrahedron Letters, 43 (14). pp. 2645-2648. ISSN 0040-4039

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The first total synthesis of the potent antifungal and cytotoxic agent (+)-crocacin D in optically pure form following a convergent strategy is described here. The regioselective ring opening of a silyl-substituted epoxide with an azide ion, based on a method developed by us earlier, and subsequent subjection of the resulting α-azido-β-hydroxyalkylsilane intermediate to a Peterson elimination reaction at an appropriate stage during the synthesis constituted the key steps for the stereoselective construction of the crucial cis enamide moiety of the molecule.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Antifungals; Cytotoxins; Aldol Reactions; Peterson Olefination; Enamide
ID Code:20597
Deposited On:20 Nov 2010 13:54
Last Modified:22 May 2011 15:43

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