A short, scalable synthesis of the carbocyclic core of the anti-angiogenic cortistatins from (+)-estrone by B-ring expansion.
A rapid and scalable synthesis of the carbocyclic core of the potent antiangiogenic natural products, the cortistatins, is presented starting from readily available (+)-estrone. Key steps include a regio- and stereoselective benzylic cyanation and a Demjanov rearrangement.
Kürti
László
L
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Czakó
Barbara
B
Corey
E J
EJ
D000146:Acids, Carbocyclic / Q000138:chemical synthesis*; D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D004970:Estrone / Q000737:chemistry*; D009479:Neuropeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000146:Acids, Carbocyclic; D020533:Angiogenesis Inhibitors; D009479:Neuropeptides; C099323:cortistatin; D004970:Estrone