Spirodiepoxide strategy to the C ring of pectenotoxin 4: synthesis of the C1-C19 sector.
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.
Joyasawal
Sipak
S
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Lotesta
Stephen D
SD
Akhmedov
N G
NG
Williams
Lawrence J
LJ
D000466:Alkadienes / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D000095702:Polyether Toxins
D000466:Alkadienes; D003300:Copper; D004852:Epoxy Compounds; D018942:Macrolides; C471226:pectenotoxin-4; D000095702:Polyether Toxins; C025947:propadiene