Journal of Organic Chemistry p. 6807 - 6813 (1993)
Update date:2022-08-04
Topics:
Chai, Ki-Byung
Sampson, Paul
Cyclohexenone 13, containing the fully elaborated taxane A ring, was prepared from 4,4-dimethyl-2-cyclohexenone (43percent for four steps); two copper-catalyzed Grignard conjugate addition reactions on crowded dienones 8 and 11 were employed as key transformations.Elaboration of 13 to the chloro keto acid 6 was achieved via an epoxidation/regioselective chloride-mediated epoxide ring opening/Jones oxidation protocol (42percent for three steps).Macrolactonization (59percent) followed by chemoselective transannular aldol condensation within the resulting 11-membered bicyclic keto lactone 4 under thermodynamic control (51percent) resulted in closure of the taxane B ring to afford the target 2(5H)-furanone 3.
View MoreAnhui New Star Pharmaceutical Development Co., Ltd
Contact:013956922763
Address:Floor 3, F9A, F Workshop, No.110 Kexue Road, High-Tech Development Zone, Hefei, Anhui ,China
shanghai jinshan pharmaceutical Co.,Ltd
Contact:021-57363011,13681638167
Address:No. 7966 Tingfeng Road,Jinshan,Shanghai,China
Contact:0086-29-88315623
Address:S711, Innovation Bldg No.25 Gaoxin 1st Rd, Xian P.R of China 710075
Yantai Derun Liquid Crystal Materials Co. Ltd.
website:http://www.ytderun.com
Contact:86-535-6300169
Address:ROOM 90, XIANGFU STREET, FUSHAN NEW-HIGH-TECH IDUSTRY ZONE, YANTAI
Hangzhou LINGEBA Technology Co., Ltd.
Contact:+0086-571-87389059
Address:Office 1-913,NewYouth Plaza, GongShu Area, HangZhou,ZheJiang,P.R.China
Doi:10.1016/0008-6215(93)84024-Z
(1993)Doi:10.1016/0223-5234(93)90030-I
(1993)Doi:10.1002/cctc.201501153
(2016)Doi:10.1007/BF00863378
(1992)Doi:10.1016/j.tetlet.2013.12.002
(2014)Doi:10.1021/jo01266a012
(1968)