Total Synthesis of GracilioetherF: Development and Application of Lewis Acid Promoted Ketene-Alkene [2+2]Cycloadditions and Late-Stage CH Oxidation

The first synthesis of gracilioetherF, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene-alkene [2+2]cycloaddition and a late-stage carboxylic acid directed C(sp3)H oxidation. T...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie Vol. 126; no. 52; p. 14750
Main Authors Rasik, Christopher M, Brown, M Kevin
Format Journal Article
LanguageGerman
Published Weinheim Wiley Subscription Services, Inc 22.12.2014
Subjects
Chemistry
Oxidation
Online AccessGet full text

Cover

More Information
Summary:The first synthesis of gracilioetherF, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene-alkene [2+2]cycloaddition and a late-stage carboxylic acid directed C(sp3)H oxidation. The synthesis requires only eight steps from norbornadiene.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201408055