J Am Chem Soc. 2006 Feb 1;128(4):1048-9.

Total synthesis of garsubellin A.

Source

Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, New York, New York 10021, USA.

Abstract

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.

PMID:: 16433500; [PubMed - indexed for MEDLINE]

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CA28824/CA/NCI NIH HHS/United States

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