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A formal total synthesis of racemic sesquiterpenoid sativene
1Department of Chemistry, Queensborough Community College/CUNY, Bayside, New York 11364, USA. skarimi@qcc.cuny.edu
Journal of Natural Products
|April 28, 2001
Abstract:
Several key reactions involving intramolecular cyclization, Grignard reaction, and ionic hydrogenation have been employed in a formal synthesis of sativene. The synthesis affords 3-isopropyl-6-methyltricyclo[4.4.0.0(2,8)]decan-7-one, 12, McMurry's penultimate precursor to sativene, in 28% overall yield in eight steps starting with the commercially available racemic Wieland--Miescher ketone.