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Issue 19, 2018
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A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges: nakijinols A, B and E–G

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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.

Graphical abstract: A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges: nakijinols A, B and E–G

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Publication details

The article was received on 26 Mar 2018, accepted on 21 Apr 2018 and first published on 24 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00721G
Citation: Org. Biomol. Chem., 2018,16, 3639-3647
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    A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges: nakijinols A, B and E–G

    Y. Takeda, K. Nakai, K. Narita and T. Katoh, Org. Biomol. Chem., 2018, 16, 3639
    DOI: 10.1039/C8OB00721G

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