Tetrahedron p. 3491 - 3498 (1984)
Update date:2022-08-03
Topics:
Franke, L.R. Rodriguez-Avial
Wolf, H.
Wray, V.
Enones of formulae Ia-d undergo cyclization to give stereoselectively the enol esters IIa-d, respectively.IIa-d are suitable synthones for some sesquiterpene syntheses.-In this paper the synthesis of torreyol (1) is described by an all step strereocontrolled reaction sequence: cyclization educt 10 (Ic) was prepared by alkylation of 8 with 5 and enol ether cleavage of 9.The reaction sequence 11a (IIc)<*>14a 15<*>18 (ester hydrolysis, formation of the tert. alcohol, degradation of the isopropenyl group) followed by oxidation resulted in the formation of ketone 19 whose relative configuration was determined by the 2D J-resolved 400 MHz (1)H NMR spectrum.After methylation at C-8 (22<*>23) the tosylhydrazone 25 underwent Bamford-Stevens reaction to yield (+/-)-1.
View Morewebsite:http://www.shochem.com
Contact:021-50800795
Address:No.1043, Halei Rd, Zhangjiang Hi-Tech Park, Shanghai, Postcode 201203, China
Jiangxi Global Natural Spice Co., Ltd.
website:https://www.jxhqxl.com/
Contact:+86-796-8106598
Address:No.89, Wenshan Road,South Industrial Park, Jishui County,Jiangxi Province
Beijing Mesochem Technology Co.,LTD
website:http://www.mesochem.com
Contact:0086-10-57862036
Address:2301, Floor 23, Building 9 Lippo Plaza, Yard 8 Ronghua Middle Road, ETDZ, Beijing, China
CHANGZHOU HANGYU PHARMACEUTICAL TECHNOLOGY CO., LTD
website:http://www.czyys.com
Contact:0086-519-88802789
Address:No.300,Yanling Middle Road, Changzhou, Jiangsu, China
Contact:86-575-86132822，86-575-86085355
Address:No.418 Dadao West Road,Qixing Street,Xinchang, Zhejiang Province, China.
Doi:10.1002/jhet.25
(2009)Doi:10.1016/j.tetlet.2009.07.060
(2009)Doi:10.1016/j.bmcl.2007.05.102
(2007)Doi:10.1021/ol071332c
(2007)Doi:10.1021/jo070750s
(2007)Doi:10.1016/j.bmcl.2008.10.056
(2008)
