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Synthesis of the complete carbocyclic skeleton of vinigrol
Lionel Gentric1, Issam Hanna, Louis Ricard
1Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, F-91128 Palaiseau Cedex, France.
Organic Letters
|March 28, 2003
Abstract:
[reaction: see text] An efficient entry to the fully elaborated skeleton of vinigrol is described. The installation of the desired stereochemistry at C(12) and the construction of the eight-membered ring were achieved in one operation by a remarkably facile anionic oxy-Cope rearrangement of Z-isopropenyl isomer 24.