Total synthesis of (+/-)-cameroonanol.
[reaction: see text]The structure and relative stereochemistry of the novel silphiperfolane-type sesquiterpene cameroonan-7alpha-ol (1) were confirmed by a total synthesis of (+/-)-1 from 3,3,5-trimethylbicyclo[3.3.0]oct-1(8)-en-2-one (6) by means of a Sakurai reaction with (Z)-crotylsilane, free radical hydrobromination, base-induced cyclization, and LiAlH4 reduction.
Davis
C E
CE
Department of Chemistry, University of Illinois, Urbana 61801, USA.
Duffy
B C
BC
Coates
R M
RM
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D012717:Sesquiterpenes; C414391:cameroonan-7-ol