Total synthesis of garsubellin A.
A concise approach to the laboratory synthesis of garsubellin A is described. Garsubellin A, an effective inducer of choline acetyltransferase (ChAT), has been shown to have potential as a therapeutic agent for the treatment of Alzheimer's disease. Starting from 3,5-dimethoxyphenol, the synthesis has provided garsubellin A in an 18-step sequence. Notable transformations include dearomative allylation, diastereoselective vinylogous lactonization, iodocarbocyclization, transannular Wurtz, and bridgehead functionalization reactions.
Siegel
Dionicio R
DR
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, New York, New York 10021, USA.
Danishefsky
Samuel J
SJ
D029760:Garcinia / Q000737:chemistry; D013729:Terpenes / Q000138:chemical synthesis*
D013729:Terpenes; C106690:garsubellin A