Formal total synthesis of (±)-7-deoxycylindrospermopsin and its 8-epi isomer. Issue 13 (27th April 2021)

• Record Type: Journal Article
• Authors: Wang, Si-Qing; Qi, Wei-Yi; Yin, Xue-Song; Shi, Bing-Feng
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 13(2021)
• Page Start: 3360
• Page End: 3365
• Publication Date: 2021-04-27
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00381j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A concise formal synthesis of (±)-7-deoxycylindrospermopsin in 14 steps was reported. Abstract : 7-Deoxycylindrospermopsin is a member of cylindrospermopsin marine alkaloid containing a cyclic guanidine group. Herein, we present a concise formal total synthesis of (±)-7-deoxycylindrospermopsin in 14 steps from commercailly available 4-methoxypyridine. Key features of our synthetic route include the elaboration of densely functionalized piperidine via 1, 4-addition of propargylindium to enone, Sonogashira coupling to attach the pyrimidine moiety, and intramolecular conjugate addition of guanidine with alkyne to form C ring. The synthesis of its 8- epi isomer was also achieved following the same synthetic strategy.