Journal of the Chemical Society. Perkin transactions I p. 811 - 817 (1984)
Update date:2022-07-30
Topics:
Horton, Michael
Pattenden, Gerald
A new synthetic approach to cedrene (1) based on sequential inter- and intra-molecular Michael reactions using the bicyclo<3.3.0>octenone (21) as the key intermediate is described.Michael addition of the enolate derived from (21) to 2-nitrobut-2-ene, led to a mixture of diastereoisomers of the nitro ketone (22), which was then converted into the 1,4-dione (23).Treatment of (23) with potassium t-butoxide in t-butyl alcohol resulted in smooth intramolecular Michael reaction leading to a mixture of α- (24a; major) and β-isomers of the tricyclo<5.3.1.01,5>undecanedione (24) in a combined yield of 73percent.The undecanedione (24) was then converted into (+/-)-cedrene (1) and the corresponding methyl epimer (31a) via the intermediates (25), (26), (27), and (28).
View MoreSuzhou Sibian Chemical Technology Co., Ltd
website:http://www.sibianpharm.com
Contact:+8618169181984,+8618013186906
Address:Room1404,BuildingA,Jiabao Square No.323 Baodai East Road,Wuzhong District,Suzhou Jiangsu China (215128)
Changzhou Welton Chemical Co., Ltd,
Contact:0086-519-85910828,85920537,85912897
Address:No.8 Jinlong Road, Binjiang Park, Changzhou, Jiangsu, China.
Nanjing HuiBaiShi Biotechnology Co.,Ltd.
Contact:+86 (25)58745219
Address:No.606 Ningliu Road,LiuHe District.
Hebei DaPeng Pharm & Chem Co., Ltd.
Contact:86-317-7298678,0576-88861898 88861908
Address:West Songmen Village, East Songmen Town, Wuqiao, Cangzhou, Hebei ,China
Shandong Bolode Bio-Technology Co., LTD
Contact:+86-0531-58966870
Address:136 Jingyi Road,Huaiyin District,Jinan,Shandong,China
Doi:10.1007/BF00853777
()Doi:10.1021/acs.orglett.0c02956
(2020)Doi:10.1016/S0040-4039(01)01486-1
(2001)Doi:10.1080/00397910601055214
(2007)Doi:10.1016/j.jorganchem.2019.05.020
(2019)Doi:10.1021/acs.orglett.8b02295
(2018)
