This title appears in the Scientific Report :
2001
Total synthesis of (R)- and (S)-semi-vioxanthin
Total synthesis of (R)- and (S)-semi-vioxanthin
Compounds (R)- and (S)-semi-vioxanthin 2 were synthesized by a tandem Michael reaction of orsellinate 3 and the chiral Michael accepters 4. The key step for the formation of lactone (R)-4 is a regio- and enantioselective, enzyme-catalyzed reduction of tert-butyl 3,5-dioxohexanoate (5) by an alcohol-...
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Personal Name(s): | Drochner, D. |
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Müller, M. | |
Contributing Institute: |
Biotechnologie 2; IBT-2 |
Published in: | European journal of organic chemistry (2001) S. 211 - 215 |
Imprint: |
Weinheim
Wiley-VCH Verl.
2001
|
Physical Description: |
211 - 215 |
Document Type: |
Journal Article |
Research Program: |
Verfahrenstechnik zur mikrobiellen Gewinnung von Primärmetaboliten |
Series Title: |
European Journal of Organic Chemistry
|
Subject (ZB): | |
Publikationsportal JuSER |
Compounds (R)- and (S)-semi-vioxanthin 2 were synthesized by a tandem Michael reaction of orsellinate 3 and the chiral Michael accepters 4. The key step for the formation of lactone (R)-4 is a regio- and enantioselective, enzyme-catalyzed reduction of tert-butyl 3,5-dioxohexanoate (5) by an alcohol-dehydrogenase from Lactobacillus brevis. Compound (S)-4 was synthesized by the Claisen condensation of tert-butyl acetate and ethyl (S)-3-hydroxy-butanoate (8). Cleavage of the benzyloxymethyl groups in the protected (R)- and (S)semi-vioxanthins was achieved by hydrogenolysis to afford (R)-2 and (S)-2, respectively. |