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J Org Chem. 2003 Dec 12;68(25):9687-93.

Synthesis of cryptophycins via an N-acyl-beta-lactam macrolactonization.

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  • 1Department of Medicinal Chemistry and Department of Molecular Biosciences, University of Kansas, Lawrence, Kansas 66045, USA.

Abstract

An efficient and concise approach to the synthesis of the macrolide core of the cryptophycins has been developed. A novel macrolactonization utilizing a reactive acyl-beta-lactam intermediate incorporates the beta-amino acid moiety within the 16-membered macrolide core. This modular approach, involving a cyanide-initiated acyl-beta-lactam ring opening followed by cyclization, was successfully applied to the total synthesis of cryptophycin-24. The strategy was also used in an efficient synthesis of the 6,6-dimethyl-substituted dechlorocryptophycin-52. In this case, the cyanide-initiated ring opening of the bis-substituted 2-azetidinone followed by macrolactonization was achieved through a catalytic process.

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