Stereocontrolled total synthesis of fucoxanthin and its polyene chain-modified derivative.

Organic letters (2012-01-20)
Takayuki Kajikawa, Satoshi Okumura, Takashi Iwashita, Daisuke Kosumi, Hideki Hashimoto, Shigeo Katsumura

Fucoxanthin exhibits high energy transfer efficiencies to Chlorophyll a (Chl a) in photosynthesis in the sea. In order to reveal how each characteristic functional group, such as the length of the polyene chain, allene, and conjugated carbonyl groups, of this marine natural product are responsible for its remarkably efficient ability, the total synthesis of fucoxanthin by controlling the stereochemistry was achieved. The method established for fucoxanthin synthesis was successfully applied to the synthesis of the C42 longer chain analogue.

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Fucoxanthin, carotenoid antioxidant