Elaboration of Sterically
Hindered δ‑Lactones
through Ring-Closing Metathesis: Application to the Synthesis of the
C1–C27 Fragment of Hemicalide

Lecourt, Camille; Boinapally, Srikanth; Dhambri, Sabrina; Boissonnat, Guillaume; Meyer, Christophe; Cossy, Janine; Sautel, François; Massiot, Georges; Ardisson, Janick; Sorin, Geoffroy; Lannou, Marie-Isabelle

doi:10.1021/acs.joc.6b02208.s001

Elaboration of Sterically Hindered δ‑Lactones through Ring-Closing Metathesis: Application to the Synthesis of the C1–C27 Fragment of Hemicalide

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posted on 2016-11-07, 00:00 authored by Camille Lecourt, Srikanth Boinapally, Sabrina Dhambri, Guillaume Boissonnat, Christophe Meyer, Janine Cossy, François Sautel, Georges Massiot, Janick Ardisson, Geoffroy Sorin, Marie-Isabelle Lannou

The synthesis of the C1–C27 fragment of hemicalide, a marine metabolite displaying a unique potent antiproliferative activity, has been accomplished. The synthetic approach highlights a remarkably efficient ring-closing metathesis reaction catalyzed by Nolan ruthenium indenylidene complexes to elaborate the highly substituted δ-lactone framework.

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ring-closing metathesis reaction Sterically Application Lactone Elaboration Fragment Hemicalide approach synthesis fragment Nolan ruthenium indenylidene complexes hemicalide δ- lactone framework marine metabolite Hindered antiproliferative activity Ring-Closing Metathesis Synthesi

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Elaboration of Sterically Hindered δ‑Lactones through Ring-Closing Metathesis: Application to the Synthesis of the C1–C27 Fragment of Hemicalide

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