74016-87-8Relevant academic research and scientific papers
Synthetic studies on polymaxenolides: Synthesis and structure elucidation of nominal epoxyafricanane and other africane-type sesquiterpenoids
Matsuda, Yutaka,Endo, Yusuke,Saikawa, Yoko,Nakata, Masaya
, p. 6258 - 6263 (2011)
A racemic total synthesis of the sesquiterpenoid unit of the hybrid marine natural product polymaxenolide has been achieved based on a three-component assembly followed by ring-closing metathesis as the key steps. However, the spectral data of our product synthesized from Δ9(15)-africanene by epoxidation were not identical with those of the natural product named epoxyafricanane. The structure confirmation of the synthetic nominal epoxyafricanane is described.
Scalable Syntheses and Biological Evaluation of Africane-Type Sesquiterpenoids
Matsuda, Yutaka,Koyama, Takayuki,Kawano, Sayaka,Miura, Kazuki,Simizu, Siro,Saikawa, Yoko,Nakata, Masaya
, (2022/02/16)
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.
