Novel synthetic approach to the 8,10-dimethyl anti-syn-anti-perhydrophenanthrene skeleton.
[reaction: see text] An efficient and highly stereocontrolled approach to the 8,10-dimethyl anti-syn-anti-perhydrophenanthrene carbon skeleton starting with the Wieland-Miescher ketone is described. The approach centers on a Diels-Alder-angular methylation-deoxygenation sequence.
Coltart
Don M
DM
The Laboratory for Bioorganic Chemistry, The Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.
Danishefsky
Samuel J
SJ
D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007659:Ketones; D010616:Phenanthrenes