A formal total synthesis of racemic sesquiterpenoid sativene.
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.
Karimi
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Department of Chemistry, Queensborough Community College/CUNY, Bayside, New York 11364, USA. skarimi@qcc.cuny.edu
D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis; D013237:Stereoisomerism
D012717:Sesquiterpenes; C430146:sativene