Total synthesis of (+)-crocacin A

Chakraborty, Tushar K. ; Laxman, Pasunoori (2003) Total synthesis of (+)-crocacin A Tetrahedron Letters, 44 (27). pp. 4989-4992. ISSN 0040-4039

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Total synthesis of the potent antifungal and cytotoxic agent (+)-crocacin A is described. The crucial (Z)-5,6-enoic amide moiety in this molecule was built by stereoselective partial reduction of a skipped diyne precursor. The diene, thus obtained, was transformed into a silyl epoxide that was regioselectively opened with an azide ion to furnish an α-azido-β-hydroxyalkylsilane intermediate. Peterson elimination of this β-hydroxysilane component in the final step resulted in the formation of the (Z)-8,9-enamide moiety of the molecule leading to a successful completion of its total synthesis.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Antifungal; Cytotoxin; Aldol Reaction; Peterson Olefination; Enamide; Crocacin
ID Code:20584
Deposited On:20 Nov 2010 14:16
Last Modified:22 May 2011 15:11

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