Angewandte Chemie - International Edition p. 17161 - 17167 (2018)
Update date:2022-08-04
Topics:
Yoshimura, Fumihiko
Itoh, Ryusei
Torizuka, Makoto
Mori, Genki
Tanino, Keiji
Brasilicardins, bacterial diterpenoid natural products that display highly potent immunosuppressive activity, are promising immunosuppressant drug candidates. Structurally, they can be described as hybrids of terpenoids, amino acids, and saccharides, and share a characteristic highly strained anti-syn-anti-fused perhydrophenanthrene terpenoid scaffold (ABC-ring system) with two quaternary asymmetric carbon atoms. A unified and stereoselective total synthesis of all four brasilicardins has been designed based on the strategic use of an intramolecular conjugate addition. The ABC-ring system was initially constructed with high stereocontrol by novel intramolecular conjugate additions of Weinreb amides and in situ generated (Z)-vinyl copper species. The late-stage common intermediate was subjected to stereoselective installation of the amino acid component, followed by introduction of the saccharide unit via glycosylation to accomplish the total synthesis of brasilicardins A–D. Our synthesis offers opportunities to synthesize various brasilicardin analogues for biological and pharmacological investigations.
View MoreHangzhou TJM Chemical Trade Co., Ltd
Contact:86-571-88223276 86-13388481653
Address:2221#,Boyuexuan,1860# Binsheng Road,Binjiang District, Hangzhou CityZhejiang Province, 310051, P. R. China
Contact:+86-371-86058576
Address:NO.32, Jingsan Road, Zhengzhou, China
SHANGHAI T&W PHARMACEUTICAL CO., LTD.
website:http://www.trustwe.com
Contact:+86-21-61551611
Address:601, No. 1, 2277 Nong, Zu Chongzhi Road, Zhangjiang Hightech. Park, Pudong
Rudong Zhenfeng Yiyang Chemical Co., Ltd.
Contact:0513-84573047
Address:South Fengli Town, Rudong County, Jiangsu 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)
Doi:10.1021/jm00126a011
(1989)Doi:10.1016/j.ica.2009.08.006
(2009)Doi:10.1002/anie.200904715
(2009)Doi:10.1021/acs.oprd.8b00400
(2019)Doi:10.1016/j.tetlet.2009.09.149
(2009)Doi:10.1021/ja9071964
(2009)