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.
Shanghai Yuanye Bio-Technology Co., Ltd.
website:http://www.shyuanye.com
Contact:+86-21-61845781
Address:Building 6, No. 465, Changta Road,Songjiang District,Shanghai,China
Zhejiang Chemline International Co., Ltd.
Contact:+86-571-88062298
Address:Hengdian Industry Area, Dongyang, Zhejiang, China
Xinjiang Zhongtai Chemical Co., Ltd.
Contact:+86-991-8788172
Address:NO.78 XISHAN RD.URUMQI，CHINA
Huaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
Shanghai Mintchem Development ., Ltd
Contact:0086 21 5190 8570
Address:R602,4#,89Nong, Mudan Road Pudong Shanghai China
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)
