Absolute configuration of eschscholtzxanthin |
| |
Authors: | A.G. Andrewes G. Engler G. Borch H.H. Strain S. Liaaen-Jensen |
| |
Affiliation: | 1. Organic Chemistry Laboratories, Norwegian Institute of Technology, University of Trondheim, N-7034 Trondheim-NTH, Norway;2. Central Research Units, F. Hoffmann-La Roche & Co. Ltd., CH-4002, Basle, Switzerland;3. Chemistry Department A, Technical University of Denmark, DK-2800, Lyngby, Denmark;4. |Chemistry Division, Argonne National Laboratory, 9700 South Cass Avenue, Argonne, IL 60439, U.S.A. |
| |
Abstract: | The chirality of eschscholtzxanthin (all-trans (3S,3′S)-4′,5′-didehydro-4,5′-retro-β,βcarotene-3,3′-diol) at 3,3′ was assigned from the CD correlation of the natural material and the semi-synthetic carotenoid prepared by (NBS-dehydrogenation of natural zeaxanthin ((3R,3′R)-β,β-carotene-3,3′-diol). The δ6(6′)-trans configuration followed from 1H NMR evidence, including nuclear Overhauser experiments with rhodoxanthin, retrodehydro-carotene (4′,5′-didehydro-4,5′-retro-β,β-carotene) and smaller retro model compounds revealing a general preference for the δ6-trans configuration in retro compounds. Biosynthetic considerations are made. |
| |
Keywords: | Papaveraceae carotenoid eschscholtzxanthin absolute configuration. |
本文献已被 ScienceDirect 等数据库收录! |
|