A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.
A stereocontrolled synthesis of a complex pentacycle embodying the molecular architecture of the cortistatin class of natural products was achieved from the (+)-Hajos-Parrish ketone. The cornerstone of our approach is a hypervalent iodine induced tandem intramolecular oxidative dearomatization and nitrile oxide cycloaddition. The manner in which these ring formations were orchestrated has yielded a rather concise strategy for synthesis.
Frie
Jessica L
JL
Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, New Jersey 08544, USA.
Jeffrey
Christopher S
CS
Sorensen
Erik J
EJ
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009479:Neuropeptides / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D009479:Neuropeptides; C099323:cortistatin; D007455:Iodine