Total synthesis of (+)-pinnatoxin A

Journal of the American Chemical Society
Craig E Stivala, Armen Zakarian

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.

Citations

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Related Concepts

Pinnatoxin A
Plant alkaloid
Spiro Compounds
Molecular Stereochemistry
Acids, Acyclic
Gene Rearrangement
Adjacent
Closed Treatment of Pelvic Ring Fracture, Dislocation, Diastasis or Subluxation; Without Manipulation
Core
Pinnatoxin A

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