Steroids p. 113 - 122 (1989)
Update date:2022-08-02
Topics:
Tal, Daniel M.
The synthesis in improved yields of one 6,7-epoxide and three 6,7-dihydroxycanrenone derivatives is described.Canrenone was the starting material for all derivatives and was obtained by acid-catalyzed lactonization of potassium canrenoate.The epoxidation of canrenone to 6α,7α-epoxycanrenone by m-chloroperbenzoic acid was improved by addition of a free radical inhibitor.This epoxide was efficiently cleaved to 6β,7α-dihydroxy-6,7-dihydrocanrenone by perchloric acid in a dioxane-water mixture; 6β,7β- and 6α,7α-dihydroxy-6,7-dihydrocanrenone were obtained by OsO4 oxidation of canrenone in ether-pyridine and subsequent reduction of the osmates by hydrogen sulfide.The stereochemistry of the products obtained from the reaction of osmium tetroxide with the 6,7-double bond of steroidal 4,6-dien-3-ones has been a controversial issue for some time.A detailed proton-NMR study of the three diol derivatives unequivocally confirmed the proposed stereochemical structure.
View MoreShanghai Bocimed Pharmaceutical Co., Ltd.
website:http://www.bocimed.com
Contact:+86-21-68861632
Address:Building 1, Lane 647, Songtao Road, Zhangjiang High-Tech Park, Shanghai
Shanghai Yuking Water Soluble Material Tech Co., Ltd
Contact:86-21-68286299
Address:4F, 13B, No. 600, South Xinyuan Road 201306, Shanghai, China
Contact:852-27701081
Address:Room 2509, New Tech Plaza, 34 Tai Yau St., San Po Kong, HK
Shanghai birch chemical technology co.,ltd
Contact:+86-21-54096810
Address:No.2588,Jungong Road,Shanghai,China
website:http://www.synchemie.com/
Contact:+86-574-87642758
Address:Room 901, Yinyi Bund Building， 132 Renmin Road
Doi:10.1016/j.tet.2006.08.084
(2006)Doi:10.1021/ja01588a027
(1956)Doi:10.1111/j.1747-0285.2011.01102.x
(2011)Doi:10.1016/j.tetlet.2008.12.056
(2009)Doi:10.1021/ic802396g
(2009)Doi:10.1107/S0108270198015893
(1999)
