Synlett

Synthetic approach to pondaplin and highly strained ansa macrolides: The dramatic influence of a fluorine atom on the efficiency of ring-closing metathesis

C Bressy, O Piva

Index: Bressy, Cyril; Piva, Olivier Synlett, 2003 , # 1 p. 87 - 90

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Citation Number: 8

Abstract

Abstract Ring-closing metathesis has been applied to the synthesis of extremely rigid 13 to 16 membered ring lactones starting from alkenyl p-(O-allyl) cinnamates and p-(O-allyl) dihydrocinnamates. The core structure of pondaplin, a natural ansa macrolide has been prepared starting from a fluoro derivative. The presence of this atom seems to have a crucial role on the success of the RCM.