Journal of Organic Chemistry p. 4252 - 4261 (2016)
Update date:2022-09-26
Topics:
Raghavan, Sadagopan
Chiluveru, Ravi Kumar
Ganapathy Subramanian
The formal total synthesis of both the enantiomers of cyclophellitol and conduritol-B and synthesis of conduramine-B derivative have been achieved from a common intermediate, obtained by regio- and stereoselective vicinal functionalization of a diene utilizing an intramolecular sulfinyl group as a nucleophile, followed by stereoselective preparation of an allylic sulfide by reaction of vinylzinc bromide with an electrophilic α-chloro sulfide, and last by ring-closing metathesis reaction as the key steps. The sulfoxide, sulfilimine, and sulfur ylid prepared from this common intermediate have been transformed into derivatives of conduritol-B, conduramine-B, and (-)-cyclophellitol, respectively. The silyl sulfide was converted via sila-Pummerer rearrangement, hydrolysis, and reduction in an one-pot operation to a hydroxymethyl group. [2,3]-Wittig-Still rearrangement was employed for the synthesis of (+)-cyclophellitol. The potential utility of sulfur intermediates as nucleophilic and electrophilic partners in total synthesis is elegantly demonstrated.
View MoreWuhan Silworld Chemical Co.,Ltd
website:http://www.silworldchemical.com
Contact:+86-27-85613400
Address:No.198 jiangjun Road, Wuhan,China 430033
Contact:+86-21-61318535
Address:Building 29,No.2139 Xizha Road, Fengxian District, Shanghai
Shanghai agrotree chemical co.,ltd.
Contact:+86-21-50117563
Address:Room 8A,liangfeng building,No.8 dongfang RD.pudong,shanghai,China
Beijing Top Science biological technology co., LTD
Contact:+86-13439059536
Address:15-1705 jre three mile, Beijing 100000,CHINA
Chuzhou Baiao Biologhy S&T Co., Ltd.
Contact:+86-25-83212599;+86-25-83212699 13705185959
Address:Room 905, Tianzheng International Platza, No.399, Zhongyang Road ,Nanjing, Jiangsu Province, China
Doi:10.1021/jm00112a031
(1991)Doi:10.1016/j.saa.2020.119102
(2021)Doi:10.1007/s11243-011-9519-6
(2011)Doi:10.1080/00397919108020798
(1991)Doi:10.1021/ol202527g
(2011)Doi:10.1002/anie.202103192
(2021)