Total Synthesis of (+)-Pinnatoxin A
Journal of the American Chemical Society2008Vol. 130(12), pp. 3774–3776
Citations Over TimeTop 10% of 2008 papers
Abstract
A convergent enantioselective total synthesis of (+)-pinnatoxin A is described. The synthesis capitalizes on the highly diastereoselective Ireland-Claisen rearrangement of an acyclic alpha-branched allylic ester to set the quaternary stereogenic center at the core of the spiroimine ring system along with the adjacent tertiary stereocenter. The all-carbon macrocyclic ring system was formed by ring-closing metathesis.
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