A concise first total synthesis of luteoride A and luteoride B. (10th September 2022)

• Record Type: Journal Article
• Authors: Song, Jinjie; Lu, Guidong; Yang, Binquan; Bai, Mengjiao; Li, Junjie; Wang, Fusheng; Lei, Ting; Jiang, Shizhi
• Is Part Of: Tetrahedron. Volume 122(2022)
• Publication Date: 2022-09-10
• Subjects: Protecting-group-free -- Redox-neutral -- Heck-dehydration -- Gilchrist alkylation -- Hetero-diels-alder; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132933
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Simple and efficient syntheses of luteoride A and luteoride B were accomplished in just two or three simple steps implementing a protecting-group-free (PGF) and redox-neutral strategy. In the adopted approach, a practical formal alkylation and a novel Heck-dehydration reaction, both characterized by high atom economy and high regio- and stereo-selectivity ( E -isomer), were conducted. Graphical abstract: Image 1 Highlights: A simple and efficient total synthesis of luteoride A and luteoride B were achieved (both at gram-scale). A protecting-group-free and redox-neutral strategy has been used. These super-ideal synthetic strategies (100% ideality) and methodologies are potentially useful for the synthesis of other members of the luteoride compound family.