Efficient asymmetric synthesis of radicicol dimethyl ether: a novel application of ring-forming olefin metathesis.
A concise, stereospecific synthesis of radicicol dimethyl ether is presented. The strategy relies on a convergent three-stage assembly of the 14-membered lactone which has, as a key transformation, a novel ring-forming metathesis reaction utilizing a vinyl epoxide.
Garbaccio
R M
RM
The Laboratory for Bioorganic Chemistry, The Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.
Danishefsky
S J
SJ
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry*; D018942:Macrolides
D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D007783:Lactones; D018942:Macrolides; C035359:monorden