Enantiomerically pure Indoloquinolizines from tryptophane
Authors:
- 12 April 1990
- journal article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1990 (4) , 313-318
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.Keywords
This publication has 13 references indexed in Scilit:
- Tremorgenic mycotoxins: synthesis of 6-demethoxyfumitremorgin CTetrahedron Letters, 1987
- Synthesis of 3-Acetyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizineHETEROCYCLES, 1985
- Study of the Pictet-Spengler reaction in aprotic media: synthesis of the .beta.-galactosidase inhibitor, pyridindololThe Journal of Organic Chemistry, 1979
- Synthetic Studies in the Alkaloid Field. Part VI. Preparation of the Diastereoisomeric Mixtures of 1,4,6,7,12,12b-Hexahydro-3-(1-hydroxyethyl)indolo[2,3-a]quinolizines.Acta Chemica Scandinavica, 1978
- Reaktionen an Indolderivaten, XXX Die stereoselektive und stereospezifische Totalsynthese der Geissoschizin‐IsomerenEuropean Journal of Inorganic Chemistry, 1976
- Pictet-Spengler Condensations in Refluxing BenzeneHETEROCYCLES, 1976
- Reaktionen an Indolderivaten, XXV. Die stereoselektive Totalsynthese des Roxburghins DEuropean Journal of Inorganic Chemistry, 1975
- Synthesis of 1, 3-Disubstituted-1, 2, 3, 4-tetrahydro-β-carboline Derivatives, and Studies on Their StereoisomersYAKUGAKU ZASSHI, 1974
- Reaktionen an Indolderivaten, XI. Die stereoselektive Totalsynthese von DL‐Ajmalicin, DL‐19‐epi‐Ajmalicin, DL‐Formosanin und IsoformosaninEuropean Journal of Inorganic Chemistry, 1969
- Reaktionen an Indolderivaten, VIII. Die partiell stereoselektive Totalsynthese von DL‐Akuammigin und DL‐TetrahydroalstoninEuropean Journal of Inorganic Chemistry, 1968