Helvetica Chimica Acta p. 1954 - 1969 (1990)
Update date:2022-08-03
Topics:
Gmuender, Michael Roman
Eugster, Conrad Hans
Starting from our recently described synthon (+)-24, the enantiomerically pure 3,6:4,5:3',6':4',5'-tetraepoxy-4,5,4',5'-tetrahydro-ε,ε-carotene (34) and its 15,15'-didehydro analogue 32 were synthesized in eleven and nine steps, respectively (Scheme 4).Chiroptical data show, in contrast to the parent ε,ε-carotene, a very weak interaction between the chiral centers at C(5), C(5'), C(6), C(6'), and the polyene system.Diisobutylaluminium hydride reduction of 32 lead rather than to the expected 15,15'-didehydro analogue 35 of cycloviolaxanthin (8), to the polyenyne 36 (Scheme 5).We explain this reaction by an oxirane rearrangement leading to a cyclopropyl ether followed by a fragmentation to an aldehyd on the one side and an enol ether on the other (Scheme 6).This complex rearrangement includes a shift of the whole polyenyne chain from C(6), C(6') to C(5), C(5') of the original molecule.
View MoreHuangshan Violet Biological Technology Co., Ltd
Contact:+86-559-2335676
Address:16-201 JinShanYuan,JiangNan New City,TunXi District,HuangShan City,AnHui Province,China
Anyang Double Circle Auxiliary CO.,LTD
Contact:0086-134 6082 4403
Address:dongfeng road, anyang city, henan province,china
JIANGSU GRAND XINYI PHARMACEUTICAL CO.,LTD
website:http://www.xypharm.com/
Contact:+86-515-84383317
Address:Chenli Road,Costal Chemical Area Binhai,Yancheng, Jiangsu,China
Contact:86-21-34622192,13917187091,21-34622765
Address:No. 500 Caobao Road Shanghai P.R China
Shanghai Longjin Metallic Material Co., Ltd.
website:http://www.shlongjin.cn/
Contact:021-56517503,56502257
Address:No.16, Lane 555, Chengyin Road, Shanghai
Doi:10.1016/S0040-4020(01)90084-5
(1990)Doi:10.1021/acs.jmedchem.9b01928
(2020)Doi:10.1055/s-0035-1562783
(2016)Doi:10.1021/jo00003a030
(1991)Doi:10.1021/jo00007a025
(1991)Doi:10.1016/j.phytol.2016.07.022
(2016)