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Abstract
Septosones B and C and spiroetherones A and B are two pairs of polycyclic avavane-type meroterpenoids which possess the same distinctive spiro[4.5]decane backbone but opposite orientations and exhibit promising biological activity. We report here the total synthesis of 1’-epi-septosones B and C and the originally assigned structures of spiroetherones A and B through an unusual stereospecific 1,2-alkyl migration of a 6/6 fused dienone tertiary alcohol to a spiro[4.5] enedione scaffold, which also led to the structural revision of spiroetherones A and B. More importantly, two new compounds were found to exhibit significant anticancer activity against Hep G2, MV-4-11, and MOLT-4 cell lines with IC50 value as low as 2.1 µM through bioactivity profiling of the synthetic advanced intermediates.
Supplementary materials
Title
Total synthesis of 1’-epi-septosones B and C and the originally assigned structures of spiroetherones A and B
Description
Septosones B and C and spiroetherones A and B are two pairs of polycyclic avavane-type meroterpenoids which possess the same distinctive spiro[4.5]decane backbone but opposite orientations and exhibit promising biological activity. We report here the total synthesis of 1’-epi-septosones B and C and the originally assigned structures of spiroetherones A and B through an unusual stereospecific 1,2-alkyl migration of a 6/6 fused dienone tertiary alcohol to a spiro[4.5] enedione scaffold, which also led to the structural revision of spiroetherones A and B. More importantly, two new compounds were found to exhibit significant anticancer activity against Hep G2, MV-4-11, and MOLT-4 cell lines with IC50 value as low as 2.1 µM through bioactivity profiling of the synthetic advanced intermediates.
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