Stereoselective synthesis of the phorboxazole A macrolide by ring-closing metathesis.
[Structure: see text] Described is a regio- and stereoselective ring-closing metathesis (RCM) to form the C2-C3 alkene of the macrolide-containing domain of phorboxazole A. This work demonstrates a dramatic effect of reaction solvent on RCM product (E/Z)-selectivity. This process offers an alternative assembly of the macrolide-containing domain of phorboxazole A, one of the most potent anticancer agents known.
Wang
Bo
B
Department of Chemistry, Institute of Technology, University of Minnesota, 207 Pleasant Street Southeast, Minneapolis, Minnesota 55455, USA.
Forsyth
Craig J
CJ
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*
D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D018942:Macrolides; D010080:Oxazoles; C408887:phorboxazole A