Tetrahedron p. 4849 - 4860 (1987)
Update date:2022-07-30
Topics:
Marshall, James A.
DeHoff, Bradley S.
The stereoselective total synthesis of (+/-)-anisomelic acid (34) has been achieved starting from aldehyde 7, the ozonolysis product of geranyl acetate.Two key steps ensured the stereoselectivity of the synthesis.The first entailed a highly anti-selective addition of the allyltitanium derived from carbamate 15 to aldehyde 5 affording the enol carbamate allylic alcohol 16.The second was a highly (Z)-selective Horner-Emmons cyclization of the derived phosphono ester aldehyde 25 leading to the conjugated ester 27.Further conversion led to the crystalline lactone 30 whose structure was confirmed through single crystal X-ray analysis.Equilibration of the conjugated double bond of 30 gave rise to a 1:1 mixture of the (Z) and (E) isomers.This result was foretold by molecular mechanics calculations.
View MoreNingxia Soochow Agrochemical Limited Company
Contact:(+86)0512 6320 8190
Address:wujiang
Contact:0571-86821378 ,86820258,56836287,56830923,
Address:Block D ,20F, Tianyuan Building,No.508, Wensan RD, 310013,Hangzhou Zhejiang China
Shandong Xinhua Pharmaceutical Co.,Ltd
website:http://www.xhzy.com
Contact:+86-533-2196801
Address:1 lutai road,zhangdian dis,Zibo City
Shanghai Hongbang Medical Technology CO.,. Ltd
Contact:13671516988 /18917636693
Address:Room1, No67 Building, Yongde Road369, Wujing Town, Minhang Districy, Shanghai CIty, China.
KangZhiYuan Pharmaceutical Company Limited
Contact:(Sabrina)86-20-85273232
Address:4th floor, building B, Dadi industry zone, Tangxia, Tianhe, Guangzhou, China
Doi:10.1021/ja106901u
(2010)Doi:10.1021/ja1064153
(2010)Doi:10.1039/c4tc01183j
(2014)Doi:10.1246/bcsj.20100033
(2010)Doi:10.1002/jhet.449
(2010)Doi:10.1039/c004873a
(2010)