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- Title
Synthese von diastereo- und enantio-selektiv deuterierten β,ε-, β,β-, β,γ- und γ,γ-Carotinen.
- Authors
Märki, Hans Peter; Eugster, Conrad Hans
- Abstract
Synthesis of Diastereo- and Enantioselectively Deuterated β,ε-, β,β-, β,γ- and γ,γ-Carotenes We describe the synthesis of (1′ R, 6′ S)-[16′, 16′, 16′-2H3]-β, εcarotene, (1 R, 1′ R)-[16, 16, 16, 16′, 16′, 16′-2H6]-β, β-carotene, (1′ R, 6′ S)-[16′, 16′, 16′-2H3]-γ, γ-carotene and (1 R, 1′ R, 6 S, 6′ S)-[16, 16, 16, 16′, 16′, 16′-2H6]-γ, γ-carotene by a multistep degradation of (4 R, 5 S, 10 S)-[18, 18, 18-2H3]-didehydroabietane to optically active deuterated β-, ε- and γ-C11-endgroups and subsequent building up according to schemes \documentclass{article}\pagestyle{empty}\begin{document}${\rm C}_{11} \to {\rm C}_{14}^{C_{\mathop {26}\limits_ \to }} \to {\rm C}_{40} $\end{document} and C11 → C14; C14+C12+C14→C40. NMR.- and chiroptical data allow the identification of the geminal methyl groups in all these compounds. The optical activity of all-( E)-[2H6]-β,β-carotene, which is solely due to the isotopically different substituent not directly attached to the chiral centres, is demonstrated by a significant CD.-effect at low temperature. Therefore, if an enzymatic cyclization of [17, 17, 17, 17′, 17′, 17′-2H6]lycopine can be achieved, the steric course of the cyclization step would be derivable from NMR.- and CD.-spectra with very small samples of the isolated cyclic carotenes. A general scheme for the possible course of the cyclization steps is presented.
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 5, p1257
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640504