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Asymmetric synthesis of the tricyclic core of cyathin diterpenoids via intramolecular Heck reaction |
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| Authors: | Emmanuelle Drè ge,Didier Desmaë le |
| Affiliation: | a Unité de Chimie Organique Associée au CNRS, Faculté de Pharmacie, 5, rue J.-B. Clément, 92290 Châtenay-Malabry, France b Laboratoire de Cristallographie Bioinorganique, Faculté de Pharmacie, 5 rue J.-B. Clément, 92296 Châtenay-Malabry, France |
| Abstract: | The enantioselective synthesis of the ketones 3 which displays the carbon core of NGF-inducing cyathane diterpenes is described. The key tricyclic trienone 22 was assembled in 13 steps from Michael adduct (R)-8a via intramolecular Heck cyclization of the chiral triflate 21. The trienone 22 was further elaborated into ketone 3 through trimethylaluminum-promoted expansion of the C-ring with trimethylsilyldiazomethane. |
| Keywords: | Terpenes and terpenoids Michael reactions Heck reactions Ring transformation Diazo compounds |
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