An efficient one-pot synthesis of 5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione from 9-bromide-11-hydroxypregna-1, 4, 16-trien-3, 20-dione by two annulation reactions.
An efficient method to prepare 5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione in one pot was reported. Treatment of 9-bromide-11-hydroxypregna-1, 4, 16-trien-3, 20-dione with Raney Ni in absolute ethanol afforded 5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione by two annulation reactions in reasonable yield. The absolute configuration was also confirmed by X-ray crystal analysis.
Jia
Ping
P
Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, PR China.
Wu
Xuling
X
Yu
Yongping
Y
Zhang
Guolin
G
D018360:Crystallography, X-Ray; D054879:Halogenation; D011281:Pregnatrienes / Q000737:chemistry*; D011282:Pregnenediones / Q000737:chemistry*; D011283:Pregnenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
C539866:5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione; C539867:9-bromide-11-hydroxypregna-1, 4, 16-trien-3, 20-dione; D011281:Pregnatrienes; D011282:Pregnenediones; D011283:Pregnenes