Baker's yeast mediated preparation of carbohydrate-like chiral synthons
β Scribed by Giovanni Fronza; Claudio Fuganti; Piero Grasselli; Stefano Servi
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 209 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Baker's yeast mediated reduction of the cc-acetoxy ketones (l)-( 2) proceeds with high enantio-and stereoselectivity to give the anti carbinols ($)-( 6), ea:ily converted into the masked chiral deoxy sugars ( 12)-( 14), --from which E-and k-deoxyzugars have been obtained.
Carbohydrates are now being used as starting materials in the synthesis of enantiomerically pure forms of natural products and drugs belonging to quite different structural 1 classes. In
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Asymmetric reduction of B-ketothioester derivatives with baker's yeast produced the cou'responding optically pure 3S-hydroxythioesters, whic.4 are useful chiral buiZdiz;a blocks in organic synthesis. The util:ity of the present method #eoseLective synthesis of sex attractant !,f pine saw-f?+, 12~,3~
The C 6' '7' C8 and C9 chiral products ( 8), ( 7), ( 14) and ( 19), containing one, two and three