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Synthesis of Galbonolide B
P. J. Parsons*, L. Pennicott, J. Eshelby, M. Goessman, A. Highton, P. Hitchcock
The University of Sussex, Brighton, Pfizer Pharmaceuticals Limited, Sandwich and AstraZeneca, Macclesfield, UK
19 March 2008 (online)
Galbonolide B is active against some pathogenic fungi. The Sussex synthesis elegantly installs the 1,6-stereogenic centers and the diene moiety in fragment C by means of an Ireland-Claisen rearrangement followed by a silicon-mediated 1,4-elimination. The creation of the macrocycle (J → K) by means of an intramolecular Claisen condensation is also noteworthy.