A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges: Nakijinols A, B and E-G

Yuki Takeda, Keiyou Nakai, Koichi Narita, Tadashi Katoh

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3639-3647
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number19
DOIs
Publication statusPublished - Jan 1 2018
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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