Struktur und Eigenschaften von 5‐ epi ‐Flavoxanthin und 5‐ epi ‐Chrysanthemaxanthin | Zendy

Cadosch Herbert | Zendy; Vögeli Ulrich | Zendy; Rüedi Peter | Zendy; Eugster Conrad Hans | Zendy

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Struktur und Eigenschaften von 5‐ epi ‐Flavoxanthin und 5‐ epi ‐Chrysanthemaxanthin

Author(s) -

Cadosch Herbert,

Vögeli Ulrich,

Rüedi Peter,

Eugster Conrad Hans

Publication year - 1978

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19780610502

Subject(s) - chemistry , polyene , stereochemistry , epoxide , cotton effect , absolute configuration , ring (chemistry) , circular dichroism , organic chemistry , catalysis

Structure and properties of 5‐ epi ‐flavoxanthin and 5‐ epi ‐chrysanthemaxanthin The absolute configurations of 5‐ epi ‐flavoxanthin ( 6 ) and 5‐ epi ‐chrysanthemaxanthin ( 7 ) prepared by acid catalysed rearrangement of semi‐synthetic lutein epoxide 5 are shown to be (3 S , 5 S , 8 R , 3′ R , 6′ R ) and (3 S , 5 S , 8 S , 3′ R , 6′ R ), respectively. Contrary to published data [5] the relationship of the polyene chain and H 3 (18) on the dihydrofurane ring is cis for the pair of stereoisomers having a Δδ = δ (HC(7)) − δ (HC(8)) = 0,22 ppm and 3 J ≡ 0. These conclusions are in full accord with the chiroptical data.

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