AbstractÐTetrahydro-b-carbolines have been prepared in a diastereomerically pure form by a short, ef®cient synthetic sequence consisting of reaction of a-aminoaldehydes with tryptamine. A study was made of the major factors affecting the stereoselectivity of the Pictet± Spengler reaction.
The pictet-spengler reaction and biogenic tryptamines: Formation of tetrahydro-β-carbolines at physiological pH
✍ Scribed by James C. Callaway; Jukka Gyntber; Antti Poso; Mauno M. Airaksinen; Jouko Vepsäläinen
- Book ID
- 118284439
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1994
- Tongue
- English
- Weight
- 405 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0022-152X
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📜 SIMILAR VOLUMES
The Pictet-Spengler(P-S) reaction of Nb-hydroxytryptamines 5 and cysteinals 6 in the presence of trifluoroacetic acid(TFA) at room temperature gave the tetracyclic compounds 7a as well as the corresponding Nb-hydroxy-S-carbolines 8. The optically active nitrones 9, isolated from the similar reaction
Under conditions of kinetic control, the cis-diastereoselectivity of the Pictet-Spmgler ~~betwecnhyptopbanestersandeldchydescenbecontrollcdbyv~ng~si~oCIbewbrgroup; the readion pmcecda in essentially quantitative yield with most aldehydg wbea tJc&acdilldllomfonu inthepresmceofmolcallarsiev~.