Journal of Organic Chemistry p. 409 - 417 (1983)
Update date:2022-08-03
Topics:
Matthews, Randall S.
Mihelich, Edward D.
McGowan, Laureen S.
Daniels, Karen
A synthesis of 11-deoxy-7-oxa prostanoids is presented.The synthesis of this new series of prostaglandin analogues commences with cis-2,3-epoxycyclopentanol (1), protected as an appropriate ether.The key step is the highly regioselective opening of that epoxide with an alkynyl alane reagent.For definition of the scope of that reaction, a brief study of the behavior of other carbon-centered nucleophiles with epoxide 1 was undertaken.It was found that only the alanyl reagent is selective in the desired direction.A rationalization for that selectivity is offered.Following the synthesis herein, over 30 analogues were prepared.Among them are eight optically pure compounds, including four isomers of 11-deoxy-7-oxaprostaglandin E1.
View MoreShanghai Yurui Biotechnology(Anyang) Pharmaceutical Co., Ltd
Contact:+86-0372-3662335 +86-0372-3661988
Address:hanling industrial park anyang
Hangzhou Yanshan Chemical Co.,Ltd.
Contact:86-571- 87698076
Address:Room 1001, #1 Building, Zhongtian MCC, No.2 Youzhinong, Wenyi West Road, Xihu District, Hangzhou, China
Tianjin Derchemist Sci-Tech Co., Ltd.
website:http://www.derchemist.com
Contact:+86-22-58627059
Address:Xinmao Science and Technology Park,Huayuan Industrial Park
website:https://www.yurisolar.com/en
Contact:+86-29-81101199
Address:No. 560, East Hangtian Road, Xi'an, China
Jinan Yijialian Economic and Trade Development Co., Ltd.
Contact:+86 0531-66729596
Address:jinan
Doi:10.1021/om300120x
(2012)Doi:10.1016/j.jfluchem.2004.04.011
(2004)Doi:10.1007/s11746-001-0218-y
(2001)Doi:10.1007/BF00846001
()Doi:10.1021/jo9722616
(1998)Doi:10.1002/macp.1973.021740105
(1973)