Tetrahedron p. 4925 - 4950 (1990)
Update date:2022-08-03
Topics:
Finch, Harry
Mjalli, Adnan M. M.
Montana, John G.
Roberts, Stanley M.
Taylor, Richard J. K.
The bicycloalkanones (1)-(3) were treated with the lithiated sulphone (4) to give the ring expanded α-methoxyketones (12), (14) and (16) generally as a mixture of epimers. The same bicycloalkanones furnished the α-benzyloxyketones (13), (15), and (17) on reaction with reagent (5). The ketone (3) reacted with the sulphone anion (6) to give, after Lewis acid treatment, the α-allyloxycyclopentanone derivatives (27a) and (27b) and one of these compounds (27b) was transformed into the ether (31). The bicycloheptanone (20) was converted into four ring-expanded products (22a), (22b), (24a) and (24b) and one of the compounds (24a) was used to synthesise the prostacyclin analogue (36). A brief study was made of the mechanism of the Lewis-acid catalysed rearrangement of the intermediate hydroxy sulphone to the ring-expanded compounds.
View MoreJinan Hongfangde Pharmatech Co.LTD
Contact:0531-88870908
Address:F Bldg,750#,Shunhua Rd,New&High-tech Zone,Jinan,Shandong,China 250101
Longhui qunfeng Chemical Co., Ltd
Contact:86-731-82173407
Address:South-east Industrial Park, Longhui County, Hunan Province, China
Beijing Apis Biotechnology Co., Ltd.
Contact:86-010-67856775-8551
Address:NO.4PUHUANGYU ROAD,FENTAI DISTRICT, BEIJING, CHINA
Zhejiang Rongkai Chemical Technology Co.,Ltd.
Contact:+86-578-8185786
Address:Shangjiang Industrial Zone,Suichang
Luoyang Aoda chemical Co.,Ltd.
Contact:+86-379-67518785 67516588
Address:MiaoWan industry district,YanShi City,Henan,China
Doi:10.1074/jbc.M111.230656
(2011)Doi:10.1007/s10847-010-9802-8
(2010)Doi:10.1021/jo200899v
(2011)Doi:10.1021/ic202747q
(2012)Doi:10.1039/c1cc11758k
(2011)Doi:10.1021/ic200701j
(2011)