## Abstract L‐Tryptophan methyl ester reacts with 1,1,3,3‐tetramethoxypropane to give methyl carbolinecarboxylate 2 as a 1:2 mixture of the (1__R__,3__S__) and (1__S__,3__S__) stereoisomers. Conversion to the corresponding amides (1__R__,3__S__)‐3 and (1__S__,3__S__)‐3 was accomplished by treatment
Enantiomerically pure Indoloquinolizines from tryptophane
✍ Scribed by Peng, Shiqi ;Winterfeldt, Ekkehard
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 691 KB
- Volume
- 1990
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
Carboline derivatives 8 and 11, obtained from L‐tryptophane methyl ester in a Pictet‐Spengler reaction with the corresponding acetals 6 and 10, add methyl vinyl ketone to form the diastereomeric mixtures 9 and 12. Under phase‐transfer conditions only 12 can be converted into a mixture of the title compounds 2a and 2b. With potassium carbonate as catalyst, however, 2b can be converted into 2c, the enantiomer of 2a.
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## Abstract For Abstract see ChemInform Abstract in Full Text.
We have reported' the transformation of 2,3-unsaturated glycosides 1 into the respective 2,3-dideoxyhex-2-enono-1 ,Slactones 2 by oxidation with 30% hydrogen peroxide in the presence of molybdenum trioxide as catalyst, followed by dehydration of the resulting hydroperoxide 3. Other syntheses of 2 ha