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C45- and C50-Carotenoids Part7 Total synthesis of (all-E,2R,6R,2′R,6′R)- and (all-E,2R,6S,2′R,6′S)-2,2′-Bis(4-hydroxy-3-methylbut-2-enyl)-γ,γ-carotene (sarcinaxanthin)

✍ Scribed by Marc Lanz; Birgit Bartels; Hanspeter Pfander

Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
929 KB
Volume
80
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of sarcinaxanthin ((2R,6R,2′R,6′R)‐1), a symmetrical C~50~‐carotenoid with two γ‐end groups, isolated from Sarcina lutea and from Cellulomonas biazotea as major pigment, was based on the strategy C~20~ + C~10~ + C~20~ = C~50~ using camphoric acid as starting material for the C~20~‐end group 3. The key step of the synthesis is a ring enlargement of the cyclopentane derivative 10 with 2,4,4,6‐tetrabromocyclohexa‐2,5‐dien‐1‐one (TBCO) to give the cyclohexane derivative 11 (Scheme 1). The spectroscopic data of the synthetic compound are in full agreement with the data of the isolated product and give the final proof for the (2R,6R,2′R,6′R) chirality of natural sarcinaxanthin.

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