653573-91-2Relevant academic research and scientific papers
Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity
Araki, Hiroshi,Inoue, Munenori,Suzuki, Takeyuki,Yamori, Takao,Kohno, Michiaki,Watanabe, Kazuhiro,Abe, Hideki,Katoh, Tadashi
, p. 9866 - 9881 (2008/09/18)
Enantioselective total synthesis of (+)-ottelione A (1) and (-)ottelione B (2), novel and potent antitumor agents from a freshwater plant, and (+)-3-epi-ottelione A (3), the earlier proposed stereostructure of 1, was efficiently achieved starting from the
Enantioselective Total Synthesis of 3-epi-Ottelione A
Araki, Hiroshi,Inoue, Munenori,Katoh, Tadashi
, p. 2401 - 2403 (2007/10/03)
An enantioselective total synthesis of (+)-3-epi-ottelione A (2), the earlier proposed stereostructure of the antitumor natural product ottelione A (4), was achieved for the first time starting from the known tetracyclic compound 9. The synthesis involves the following three crucial steps: (i) a coupling reaction of aldehyde 8 and aryllithium 7 to introduce the aromatic portion, (ii) base-induced lactol-opening/epimerization at the C1 position of 6 to deliver the requisite hydrindane 15, and (iii) Corey-Winter's reductive olefination of the cyclic thiocarbonate 19 to install the C5-C6 double bond.
