Zuidema Daniel R, Jones Paul B
Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
J Nat Prod. 2005 Apr;68(4):481-6. doi: 10.1021/np049607+.
Cyercene A has been synthesized and converted to placidene A and isoplacidene A through photoisomerization with sunlight. Hydroperoxide, isolated form Placida dendritica, was synthesized both by singlet oxygenation of cyercene A using Rose Bengal and through the irradiation of cyercene A alone in aerobic solution. The observation that hydroperoxide could be made by singlet oxygenation of cyercene A and that this occurs when cyercene A alone is irradiated supported the hypothesis that gamma-pyrones may act as triplet sensitizers. This was confirmed using cyercene A and a model gamma-pyrone to sensitize the photooxidation of n-butyl sulfide. The biosynthetic implications of these observations for Sacoglossan polypropionates are discussed.
Cyercene A已被合成，并通过阳光进行光异构化转化为placidene A和异placidene A。从Placida dendritica中分离出的氢过氧化物，既可以通过用孟加拉玫瑰红对cyercene A进行单线态氧合反应来合成，也可以通过在有氧溶液中单独照射cyercene A来合成。氢过氧化物可通过cyercene A的单线态氧合反应制得，且在单独照射cyercene A时会发生这种情况，这一观察结果支持了γ-吡喃酮可能作为三线态敏化剂的假设。使用cyercene A和一种γ-吡喃酮模型来敏化正丁基硫醚的光氧化反应，证实了这一点。本文讨论了这些观察结果对裸鳃亚目多丙酸酯生物合成的意义。
