Journal of the Chemical Society. Perkin transactions I p. 2157 - 2165 (1996)
Update date:2022-07-29
Topics:
Tanabe, Yoo
Seko, Shinzo
Nishii, Yoshinori
Yoshida, Taichi
Utsumi, Naoka
Suzukamo, Gohfu
Acid treatment of two types of aryl(gem-dihalogenocyclopropyl)methanols (ADCMs) 1 and 3 gives α- and β-halogenonaphthalenes in good yields with excellent selectivity. These alternative annulations involve two distinctive types of highly regioselective acid-induced cyclopropane ring cleavage, wherein the preferential formation of more stable cationic intermediates determines the selectivity. The stereochemical mode of both the preparation and the annulation between diastereoisomers of an ADCM has been checked. As a demonstration of this annulation, a total synthesis of each of the natural lignan lactones, justicidin E 19 and taiwanin C 20, has also been performed. Since these 4-arylnaphthalenes are expected to exhibit biological activity, the anti-platelet activating factor (anti-PAF) activity of justicidin E has been assayed.
View MoreShanghai shibo Chemical Co., Ltd
Contact:+86-021-60753516
Address:688 Qiushi Road, Jinshan High-tech Park, Shanghai, China,201512
Baoding City Light Industry And Textiles Imp.& Exp. Corp. Chemical Department.
Contact:86-312-3262436
Address:NO.658 CHAOYANG SOUTH STREET,BAODING CITY HEBEI CHINA
Nanjing Yuance Industry&Trade Co., Ltd.
website:http://www.njyuance.cn/
Contact:+86-25-85439097
Address:B1702, Aoti Bldg, No. 130, Aoti Avenue, Nanjing, China
LIANYUNGANG YC FINE CHEMICAL CO., LTD
Contact:+86-518-858 99188
Address:Shangdong Modern Bldg, South Greenpark Road, Lianyungang, Jiangsu Pro. China
Contact:+ 86 512 52491118
Address:1 Fuyu Road, Haiyu TownChangshu, Jiangsu, China
Doi:10.1002/chir.22981
(2018)Doi:10.1007/BF00598999
(1990)Doi:10.1016/S0040-4039(01)80061-7
(1984)Doi:10.3987/COM-11-12176
(2011)Doi:10.1002/ejoc.201100219
(2011)Doi:10.1055/s-0032-1317474
(2012)
