- Process for preparing carotenoid polyene chain compounds and intermediates for preparing the same
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The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.
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- A highly efficient chain-extension process in the systematic syntheses of carotenoid natural products
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Successive elongation by a C5 unit is possible when an allylic sulfone is couple with 4-bromo-3-methyl-2-butenyl phenyl sulfide (1). The thiosulfone compound formed was then oxidized to the corresponding disulfone, which, upon coupling with another equivalent of 1 and oxidation, produced the trisulfone 2, again elongated by a C5 unit (see scheme). This process, which can be repeated again, is the basis for a highly efficiently synthesis of carotenoids.
- Ji, Minkoo,Choi, Hojin,Park, Minsoo,Kee, Minyong,Jeong, Young Cheol,Koo, Sangho
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p. 3627 - 3629
(2007/10/03)
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