Scalable Syntheses and Biological Evaluation of Africane-Type Sesquiterpenoids

Yutaka Matsuda, Takayuki Koyama, Sayaka Kawano, Kazuki Miura, Siro Simizu, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticlepeer-review

Abstract

Practical total syntheses of africane-type sesquiterpenoids were realized by reexamination of a divergent strategy employing optimized three-component coupling followed by ring-closing metathesis and substrate-controlled cyclopropanation. This sequential eight-step conversion provided Δ9(15)-africanene, a common bicyclo[5.3.0]decane intermediate for the syntheses of africane derivatives, in more than twice the yield as in the previous approach. The scalability and robustness of this improved synthetic route were confirmed by gram-scale preparation of Δ9(15)-africanene. In vitro cell-based assays of the synthesized africane-type sesquiterpenoids disclosed that ester-incorporating derivatives showed cytotoxic activity against HeLa cells. The effect of relative and absolute configuration of africane-9,15-diol monoacetates on the cytotoxicity against HeLa cells was also investigated.

Original languageEnglish
Article numbere202100890
JournalChemistry and Biodiversity
Volume19
Issue number3
DOIs
Publication statusPublished - 2022 Mar

Keywords

  • africane
  • cytotoxicity
  • gram-scale synthesis
  • natural product
  • sesquiterpenoid

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • Chemistry(all)
  • Molecular Medicine
  • Molecular Biology

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