A simple and efficient total synthesis of anticancer indole alkaloids TMC-205 and its analogues. (22nd June 2021)

• Record Type: Journal Article
• Authors: Li, Tao; Song, Jinjie; Wang, Lihua; Lei, Ting; Jiang, Shizhi; Wang, Fusheng
• Is Part Of: Tetrahedron letters. Volume 74(2021)
• Publication Date: 2021-06-22
• Subjects: Anticancer -- Indole alkaloid -- Heck reaction -- Protecting-group-free -- Pinnick oxidation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153137
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A concise and efficient total synthesis of TMC-205 is achieved. A protecting-group-free and redox-economical strategy has been used. This practical reaction was further applied to the synthesis of TMC-205 analogues. Abstract: A concise synthesis of TMC-205 was accomplished in two steps via a protecting-group-free (PGF) and redox-economical strategy. In this approach, a high yield Pinnick oxidation and a practical Heck-dehydration reaction with high atom economy as well as a high regio- and stereo-selectivity ( E -isomer) were used and further applied to the total synthesis of its active analogues. This newly established route would be beneficial for future structure–activity relationship (SAR) and biological studies. The synthetic strategy and methodologies demonstrated in this paper could be extended to related biologically active natural products.