C-45-CAROTENOIDS AND C-50-CAROTENOIDS .8. SYNTHESIS OF (ALL-E,2S,2'S)-BACTERIORUBERIN, (ALL-E,2S,2'S)-MONOANHYDROBACTERIORUBERIN, (ALL-E,2S,2'S)-BISANHYDROBACTERIORUBERIN, 'R)-3,4,3',4'-TETRAHYDROBISANHYDROBACTERIORUBERIN, AND (ALL-E,S)-2-ISOPENTENYL-3,4-DEHYDRORHODOPIN

Authors
LAKOMY I SARBACH D TRABER B ARM C ZUBER D PFANDER H NOACK K
Citation
I. Lakomy et al., C-45-CAROTENOIDS AND C-50-CAROTENOIDS .8. SYNTHESIS OF (ALL-E,2S,2'S)-BACTERIORUBERIN, (ALL-E,2S,2'S)-MONOANHYDROBACTERIORUBERIN, (ALL-E,2S,2'S)-BISANHYDROBACTERIORUBERIN, 'R)-3,4,3',4'-TETRAHYDROBISANHYDROBACTERIORUBERIN, AND (ALL-E,S)-2-ISOPENTENYL-3,4-DEHYDRORHODOPIN, Helvetica Chimica Acta, 80(2), 1997, pp. 472-486
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
80
Issue
2
Year of publication
1997
Pages
472 - 486
Database
ISI
SICI code
0018-019X(1997)80:2<472:CAC.SO>2.0.ZU;2-D
Abstract
Starting from (R)-3-hydroxybutyric acid ((R)-10) the C-45- and C-50-ca rotenoids (all-E,2S,2'S)-bacterioruberin (1), (all-E,2S,2'S)-monoanhyd robacterioruberin (2), (all-E,2S,2'S)-bisanhydrobactarioruberin (3), 2 'R)-3,4,3',4'-tetrahydrobisanhydrobacterioruberin (5), and (all-E,S)-2 -isopentenyl-3,4-dehydrorhododopin (6) were synthesized. By comparison of the chiroptical data of the natural and the synthetic compounds, t he (2S)- and (2'S)-configuration of the natural products 1-3 and 6 was established.