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- W2201202317 abstract "Publisher Summary The bacterial bicyclic C 5o carotenoids exhibit two extra C 50 isoprene units substituting the C-2 and C-2' centers of the cyclohexyl rings. Three bicyclic C 50 carotenoids are known: (1) decaprenoxanthin from Flavobacterium dehydrogenans with two substituted, (2) ɛ-end groups, from Corynebacterium poinsettiae with two substituted β-end groups, and (3) sarcinaxanthin from Sarcina lutea with two substituted γ -end groups. From a biosynthetic point of view, lycopene is thought to be the immediate precursor of these carotenoids as for C 4o carotenoids: the cyclization reaction is believed to be biogenetically initiated by an electrophilic attack of a C 5 unit at the C-2, C-2' centers of the acyclic C 4o precursor. In agreement with such a postulated prenylation-cyclization process and prompted by progress in laboratory acid-promoted alkylation reactions, this chapter develops and discusses a biomimetic approach to the synthesis of these three C 5o bicyclic carotenoids. A multistep synthesis of racemic sarcinaxanthin is described using step an acid-promoted electrophilic alkylationcyclization of geranyl acetate with either isoprene epoxide or with 2-methyl-3-buten-2-ol." @default.
- W2201202317 created "2016-06-24" @default.
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- W2201202317 date "1992-01-01" @default.
- W2201202317 modified "2023-09-27" @default.
- W2201202317 title "[9] C50 bicyclic carotenoids: Sarcinaxanthin synthesis" @default.
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- W2201202317 doi "https://doi.org/10.1016/0076-6879(92)13113-c" @default.
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