Total Synthesis of 1'-epi-Septosones B and C and Discovery of Novel Compounds with Anti-Cancer Activity
Qunlong Zhang , Jingyi Kang , Tiancheng Tan , Guanjun Dong , Jianwei Chen , Zhaoyong Lu
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (18) : 2377 -2384.
Total Synthesis of 1'-epi-Septosones B and C and Discovery of Novel Compounds with Anti-Cancer Activity
Septosones B and C are a pair of polycyclic avarane-type meroterpenoids which possess a distinctive spiro[4.5]decane backbone and exhibit promising biological activity. We report here the total synthesis of 1'-epi-septosones B and C through an unusual stereospecific 1,2-alkyl migration of a 6/6-fused dienone tertiary alcohol to a spiro[4.5]enedione scaffold. More importantly, two new compounds were found to exhibit potent anti-cancer activity against Hep G2, MV-4-11, and MOLT-4 cell lines with IC50 values as low as 2.1 μM through bioactivity profiling of the synthetic advanced intermediates.
Total synthesis / Sesquiterpene quinones/hydroquinones / Meroterpenoids / Septosones / Semipinacol rearrangement / Natural products / Rearrangement
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
