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 MoreShijiazhuang Haotian Chemical Co., Ltd.
Contact:86-311-85044374
Address:293 Donggang Road
Wuxi D-Stone International Co., Ltd.
Contact:+86-510-82740567
Address:21F Hengtong Int'l Centre, 215Zhongshan Road, Wuxi, Jiangsu,China
website:http://www.chinabarton.com
Contact:+86-573-82719618
Address:No. 162 Fumin Road, Honghe Town,
Jiaxing Taixin Pharmaceutical Chemical Co., Ltd
Contact:0573-82613601
Address:Chemical Park, Jiaxing, Zhejiang, China
shanghai Tauto Biotech Co., Ltd
website:http://www.tautobiotech.com/en/index.htm
Contact:+86-21-51320588 ext. 8025
Address:No. 326, Aidisheng Rd , Zhangjiang Hi-tech Park, Shanghai , P.R.CHINA
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)
