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Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene–Alkene [2+2] Cycloadditions and Late‐Stage CH 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.