Organic Letters p. 159 - 162 (2006)
Update date:2022-08-03
Topics:
Crimmins, Michael T.
Zuccarello, J. Lucas
Cleary, Pamela A.
Parrish, Jonathan D.
(Chemical Equation Presented) 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.
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