Total synthesis of selaginellin A. (31st August 2021)

• Record Type: Journal Article
• Authors: Fujiwara, Kenshu; Itagaki, Takaya; Tokiwano, Tetsuo
• Is Part Of: Tetrahedron letters. Volume 79(2021)
• Publication Date: 2021-08-31
• Subjects: Natural product synthesis -- Diels-Alder reaction -- Natural polyphenol -- Total synthesis -- Dehydrogenative aromatization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153295
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The total synthesis of selaginellin A, isolated from Selaginella tamariscina, was achieved through an eight-step process including a Diels-Alder reaction, formation of a quinone methide moiety and dehydrogenative aromatization. The NMR spectra collected for different samples of synthetic selaginellin A initially showed irregular peak shapes and variable chemical shifts for the signals of the phenol-substituted quinone methide moiety under neutral conditions. After detailed NMR analysis, it was found that the addition of a trace amount of trifluoroacetic acid accelerated the tautomerism of the phenol-substituted quinone methide moiety and improved the reproducibility of the chemical shifts of synthetic selaginellin A.