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 MoreContact:0833-5590788/5590338/5590055
Address:Victory in the town of Red Star Village,Mount Emei City,industrial concentration area storage processing logistics parkpark
Jinan Jiaquan Chemical Co.,Ltd
Contact:+86-531-62318366
Address:Room 502 of Yidonghuayuan No.601 Huaxin Road Licheng District Jinan China
Shenzhen HwaGen Pharmaceutical Co., Ltd
website:http://www.rafflespt.com
Contact:+86-752-5538396
Address:Guangdong Huizhou China
shandong zhongke taidou chemical co.,ltd
Contact:86-531-88682301
Address:Jinan shandong Province CHina
Jiangxi Province Bethel Pharmaceutical Co., Ltd.
Contact:+86-795-259 3456 ，+86-15957688008 13566650571
Address:Huangjindui Chemical Park， Shanggao County ，Yichun city，Jiangxi Province
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)
