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  • Title: Total synthesis of (+)-pinnatoxin A.
    Author: Stivala CE, Zakarian A.
    Journal: J Am Chem Soc; 2008 Mar 26; 130(12):3774-6. PubMed ID: 18311987.
    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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