A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges: nakijinols A, B and E–G. Issue 19 (30th April 2018)

• Record Type: Journal Article
• Authors: Takeda, Yuki; Nakai, Keiyo; Narita, Koichi; Katoh, Tadashi
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 19(2018)
• Page Start: 3639
• Page End: 3647
• Publication Date: 2018-04-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00721g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Nakijinols A, B, E, F and G were efficiently synthesized via the ring closure of the N -(2-hydroxyphenyl)-formamide or -acetamide moiety. Abstract : Nakijinols A, B and analogues E through G, which are structurally unique and biologically significant sesquiterpenoid benzoxazoles, can be efficiently obtained in a highly unified manner from the sesquiterpenoid quinone, smenospongine. The starting material is accessible from the (+)-5-methyl Wieland–Miescher ketone. The synthetic method features strategic construction of the requisite dihydroxylated benzoxazole substructure via the ring closure of the N -(2-hydroxyphenyl)-formamide or -acetamide moiety. The synthesis of nakijinols is reported here for the first time. The absolute configurations of nakijinols A and E were also established.