Synthesis of cryptophycins via an N-acyl-beta-lactam macrolactonization |
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Authors: | Vidya Ramdas Eggen MariJean Nair Sajiv K Georg Gunda I Himes Richard H |
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Affiliation: | Department of Medicinal Chemistry and Department of Molecular Biosciences, University of Kansas, Lawrence, Kansas 66045, USA. |
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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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