Journal of the Chemical Society. Perkin transactions I p. 1557 - 1562 (1981)
Update date:2022-08-05
Topics:
Tokoroyama, Takashi
Fukuyama, Yoshiyasu
Kubota, Takashi
Yokotani, Kenji
The total synthesis of fraxinellone (1), the simplest example of degraded limonoid, via the 6-formyl-2,6-dimethylcyclohex-2-enecarboxylates (2) is described.In the initial approach the C-6 methylation of ethyl 6-formyl-2-methylcyclohex-2-enecarboxylate (7) was carried out by cyclopropanation and ring cleavage which unexpectedly gave the bicyclo<2.2.1>heptane compound (20), with a poor yield of the desired product.Subsequently, the key intermediate (2) was synthesized effectively by the Diels-Alder reaction between ethyl 3-methylpenta-2,4-dienoate and methacrolein.The reaction of the aldehyde ester (2) with furyl-lithium followed by double-bond isomerization with base afforded (+/-)-fraxinellone, together with the corresponding diastereoisomer.
View Morewebsite:http://www.chinacharm.cn/
Contact:86 551 5316260
Address:No. 211,XiangZhang Road,Hefei City,Anhui Province,China
Goldwills Pharmaceuticals Co., Ltd.
Contact:0916-2237889 13991621155
Address:North Suburb of Hanzhong city, Shaanxi Province
Contact:+86-574-89075960
Address:#100 Xiang Yun Road, New High tech area, Ningbo, China
Zhongshan Haihong Medicine Co., Ltd.
Contact:86-0760-86925778 （0）18824993998
Address:A7 building,lianyuan road Torch Hi-tech Industrial Development Zone
He Bei Shun Er Chemical Co., LTD.
Contact:86-0311-86996932/86860168
Address:No 18,North street
Doi:10.1016/j.tet.2004.07.089
(2004)Doi:10.1021/jo040203w
(2004)Doi:10.1021/ol048333e
(2004)Doi:10.1016/S0040-4039(01)81802-5
(1981)Doi:10.1021/jp048235a
(2004)Doi:10.1002/chem.200600009
(2006)
