Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A.
[reaction: see text] A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.
Crimmins
Michael T
MT
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, 27599, USA. crimmins@email.unc.edu
Zuccarello
J Lucas
JL
Cleary
Pamela A
PA
Parrish
Jonathan D
JD
D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
D008387:Marine Toxins; D035964:Oxocins; C076262:Brevetoxin A; D000095702:Polyether Toxins