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 MoreShijiazhuang Haotian Chemical Co., Ltd.
Contact:86-311-85044374
Address:293 Donggang Road
Kaiping Genuine Biochemical Pharmaceutical Co.,Ltd.
Contact:+86-750-2881198
Address:No.1, Xinke Road, Shatang Town, Kaiping, Guangdong Province, P.R.China
Contact:+86 021-51698675
Address:1701, Jielong Plaza, No.618 Pingliang Rd, ShangHai,China
Shanghai Rainbow Chemistry Co., Ltd.
Contact:+86-21-64968086-5815/5812
Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
Shanghai Hohance Chemical Co., ltd
Contact:13914753421
Address:Fl.5；Bld. 70, Lane 1500; Xinfei Road
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)
