15 カロチノイドの光酸化と生体内機能

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Previously, we demonstrated the photo-sensitized oxygenation of β-iond and dehydro β-ionone to dihydroactinidiolide, actinidiolide and actinidol as a model for the biosynthesis of C-11 and C-13 oxygenated compounds. In that case, a novel photo-sensitized oxidation reaction of β-ionol to allenic alcohol was found. In this paper we demonstrated the stereospecific synthesis of loiolide and isomeric allenic ketodiol by using photosensitized oxidation starting from hydroxy-β-ionol. The stereochemistry of natural and synthetic allenic compounds is discussed in view of their synthetic pathways. Vomifoliol, a novel C-13 compound isolated from Rauwolfia vomitolia was also synthesized by photo-sensitized oxygenation. The mechanisms of the formation of C-11, C-13 and C-15 compounds from carotenoids are also discussed.
天然有機化合物討論会の論文
1969-09-01