Journal of Organic Chemistry p. 7768 - 7781 (1993)
Update date:2022-08-03
Topics:
Hanessian
Tehim
Chen
The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain- extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91% ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38% overall yield.
View MoreContact:+86-20-62802632;62802633
Address:Room 330 GIGCAS Building,No.511 Kehua Street,Tianhe District
Shandong Jincheng Zhonghua Bio-pharmaceutical Co.,Ltd
Contact:+86-533-5415882
Address:Zichuan Economic Development Zone,Zibo City,Shandong Province,China
Tangshan Moneide Trading Co., Ltd.
Contact:+86-315-8309571
Address:2-7-420 Jidong Building Materials Commercial Center, Tangshan, Hebei, 064000 China
website:http://www.eastarchem.com/
Contact:1-800-898-2436
Address:1215 K Street, STE 1700
Chongqing maohuan Chemicals Co., Ltd
website:http://www.bschem.com
Contact:+86 13996103726
Address:Chongqing Nan'an District Tu Town
Doi:10.1021/acs.joc.7b01823
(2017)Doi:10.1007/s00044-012-0269-6
(2013)Doi:10.1021/ja00292a077
(1985)Doi:10.1021/jo070560h
(2007)Doi:10.1007/s00706-007-0832-x
(2008)Doi:10.1246/bcsj.80.2226
(2007)