Synthesis of the complete carbocyclic skeleton of vinigrol.
[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.
Gentric
Lionel
L
Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, F-91128 Palaiseau Cedex, France.
Hanna
Issam
I
Ricard
Louis
L
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D005658:Fungi / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; C055112:vinigrol