Chemical and Pharmaceutical Bulletin p. 1753 - 1760 (2000)
Update date:2022-09-26
Topics:
Sato
Takimoto
Mori
Total synthesis of prostaglandin F(2α) utilizing a nickel(0)-catalyzed cyclization of 1,3-diene and tethered aldehyde was achieved. The cyclization proceeded via a transmetalation of nickelacycle with dilsobutylaluminum acetylacetonate ((i)Bu2-ALAC). Thus, the reaction of 19, having a side chain corresponding to the α-chain in PGF(2α) with Ni(cod)2 (10 mol %), PPh3 (20 mol %), and 1,3-cyclohexadiene (25 mol %) in the presence of (i)Bu2-ALAC (1.5 eq) proceeded stereoselectively to give the cyclized product 26 in 54% yield. During the cyclization of 19, the Z-olefin at C-5 in the side chain completely retained its geometry, and the four contiguous chiral carbon centers in PGF(2α) were stereoselectively constructed. Transformation of the key intermediate 19 into PGF(2α) was successfully achieved.
View MoreFusilin chemical science & technology co., ltd.
Contact:532-80698166/86057573, +86-400-669-7885
Address:School of Material Science & Engineering, Shandong Uinversity of Science & Technology, Huangdao Zone, Qindao, Shandong
Suzhou Chiral Pharmaceuticals Co., Ltd.
Contact:86-0512-63197058
Address:Building A, No. 2358, Chang'an Road, Wujiang Science Park
ChangZhou XiaQing Chemical Co., Ltd.
Contact:+86-519-88721665
Address:3# Hengluo Road, Henglin Town, Changzhou City, Jiangsu Province，China
Contact:86-510-82853889
Address:Rm.3732, No.18-2,Yonghe Rd.,Wuxi,Jiangsu,214023,China
Sichuan Sangao Biochemical Co., Ltd
Contact:+86-28-84874233
Address:19F, Bldg.2, Shudu Center, Tianfu 2nd St., Hi-tech zone, Chengdu 610041, Sichuan Province, China.
Doi:10.1021/bi00587a015
(1979)Doi:10.1021/jo034719b
(2003)Doi:10.1021/jo00431a029
(1977)Doi:10.1007/BF00903814
(1976)Doi:10.1021/jo01278a054
(1967)Doi:10.1016/0040-4020(76)85192-7
(1976)
