Stereocontrolled First Total Syntheses of Amarouciaxanthin A and B

Stereocontrolled First Total Syntheses of Amarouciaxanthin A and B

The first total syntheses of amarouciaxanthin A and B (C40) via the stereoselective Wittig reaction of C15-allenic and C15-acetylenic tri-n-butylphosphonium salts with the unprecedented C25-3,8-dihydroxy-5,6-epoxyapocarotenal have been completed. Oxidation of the two hydroxyl groups in the left part...

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Veröffentlicht in:Organic letters 2013-10, Vol.15 (20), p.5310-5313
Hauptverfasser: Yamano, Yumiko, Chary, Mahankhali Venu, Wada, Akimori
Format: Artikel
Sprache:eng
Schlagworte:
Molecular Conformation
Stereoisomerism
Xanthophylls - chemical synthesis
Xanthophylls - chemistry
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Zusammenfassung:The first total syntheses of amarouciaxanthin A and B (C40) via the stereoselective Wittig reaction of C15-allenic and C15-acetylenic tri-n-butylphosphonium salts with the unprecedented C25-3,8-dihydroxy-5,6-epoxyapocarotenal have been completed. Oxidation of the two hydroxyl groups in the left part of the resulting condensation products followed by regioselective oxirane ring opening gave the target carotenoids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402540g