Spirodiepoxide strategy to the C ring of pectenotoxin 4: synthesis of the C1-C19 sector.

ABSTRACT: The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.

SUBMITTER: Joyasawal S 

PROVIDER: S-EPMC3050037 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature