32 ポリTHF環を有するトリテルペンポリエーテルの構造及び生合成仮説による全合成(口頭発表の部)

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During this decade, we have been engaged in synthetic and structural studies on highly oxidized and structurally diverse cytotoxic triterpene polyethers, which are thought to be biogenetically squalene-derived natural products (oxasqualenoids), isolated form both marine and terrestrial organisms. In particular, we have been interested in the biogenesis of polyTHF rings-containing oxasqualenoids which might be synthesized in a single step by the sequential oxacyclization from acyclic precursors squalene polyepoxides. In this symposium, we report that a novel oxasqualenoid omaezakianol (1) was isolated from the red alga Laurencia omaezakiana Masuda sp. by Suzuki et al. in 1994, and the structure including the absolute configuration has recently been found to be shown by a structural formula 6 through spectroscopic methods (Figure 1), the derivatization experiments (Scheme 1), and the asymmetric total synthesis (Scheme 2). We also report that the total synthesis of neighboring tri- and tetraTHF rings-containing teurilene (7) (Scheme 3) and (+)-omaezalcianol (6) (Scheme 4), respectively, has been accomplished on the basis of the biogenetic hypothesis (Scheme 1).
天然有機化合物討論会の論文
2007-08-24