Tetrahedron p. 687 - 694 (1992)
Update date:2022-07-30
Topics:
Boissin, Partrick
Dhal, Robert
Brown, Eric
(-)-α-Conidendrin 1 was synthesized according to a general reactionscheme that could be applied to other retrolignans as well. Thus, treatment of the optically active β-benzyl-γ-butyrolactone (R)-(+)-4 with NBS, followed with benzyl alcohol, selectively introduced a benzyloxy group in the benzylic position and afforded the mixture of epimers 7. α-Alkylation of the lithium enolate of the corresponding silyl ethers 10, with O-benzylvanillyl bromide 11, gave the trans disubstituted lactones 13 (2 epimers). Catalytic hydrogenolysis (Pd-C) of 13 selectively split the aryl benzyl ether linkage, and gave the compounds 14. Intramolecular Friedel-Crafts cyclization of the latter, using the benzyloxy group as the leaving group, was induced with BF3-Et2O and afforded (-)-α-conidendrin 1 in 36% overall yield from methyl α-vanillylhemis uccinate (R)-(+)-17.
SHANXI JINJIN CHEMICAL INDUSTRIAL CO.,LTD
website:http://www.jinjingroup.com
Contact:86-574-13989382828
Address:Economic And Technological Development Zone,Hejin?City,Shanxi Province?,China
Huaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
Nanjing Yuance Industry&Trade Co., Ltd.
website:http://www.njyuance.cn/
Contact:+86-25-85439097
Address:B1702, Aoti Bldg, No. 130, Aoti Avenue, Nanjing, China
Daqing New Century Fine Chemical Co., Ltd.(expird)
Contact:010-57126694
Address:No.39, jinxing cun, honggang district
Hangzhou Mole's Science & Technology Co.,Ltd.(expird)
Contact:+86-571-56880228
Address:15F Guodu development Building, NO.182 Zhaohui Road
Doi:10.3762/bjoc.10.42
(2014)Doi:10.1002/cbdv.201200005
(2012)Doi:10.1021/jo301817w
(2012)Doi:10.1021/om300657z
(2012)Doi:10.1055/s-0031-1290988
(2012)Doi:10.1016/j.tet.2012.08.084
(2012)
