Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene–Alkene [2+2] Cycloadditions and Late‐Stage CH Oxidation | Zendy

Rasik Christopher M. | Zendy; Brown M. Kevin | Zendy

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Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene–Alkene [2+2] Cycloadditions and Late‐Stage CH Oxidation

Author(s) -

Rasik Christopher M.,

Brown M. Kevin

Publication year - 2014

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201408055

Subject(s) - ketene , stereocenter , alkene , chemistry , cycloaddition , lewis acids and bases , total synthesis , norbornadiene , stereochemistry , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis

The first synthesis of gracilioether F, 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(sp 3 )H oxidation. The synthesis requires only eight steps from norbornadiene.

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