TY - JOUR
T1 - A novel approach to sesquiterpenoid benzoxazole synthesis from marine sponges
T2 - Nakijinols A, B and E-G
AU - Takeda, Yuki
AU - Nakai, Keiyo
AU - Narita, Koichi
AU - Katoh, Tadashi
N1 - Funding Information:
This study was financially supported by a JSPS KAKENHI (Grant Number JP15K07865) and a Grant-in-Aid for the Strategic Research Foundation Program at Private Universities (Grant Number S15110010L) from MEXT.
Publisher Copyright:
© 2018 The Royal Society of Chemistry.
PY - 2018
Y1 - 2018
N2 - 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.
AB - 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.
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U2 - 10.1039/c8ob00721g
DO - 10.1039/c8ob00721g
M3 - Article
C2 - 29708256
AN - SCOPUS:85047196586
SN - 1477-0520
VL - 16
SP - 3639
EP - 3647
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 19
ER -
