Synthesis of the two enantioners of a tetrahydro-β-carboline fromL-(–)-tryptophan

1 January 1983

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications

No. 20,p. 1147-1149
https://doi.org/10.1039/c39830001147

Abstract

Pictet–Spengler condensations of methyl 4-formyl-2,2-bis(phenylthio)butyrate with tryptophanamide and N^b-benzyltryptophanamide are stereospecific; dehydration of the adducts [(CF₃CO)₂O] followed by cyanide elimination (NaBH₄) yields tetrahydro-β-carbolines of opposite absolute confugurations, in high optical purities as demonstrated by n.m.r. examination of their methoxy-mandelamides.

Keywords

YIELDS TETRAHYDRO
CARBOLINE FROML
NB BENZYLTRYPTOPHANAMIDE
OPPOSITE ABSOLUTE
TWO ENANTIONERS
SPENGLER CONDENSATIONS
METHOXY MANDELAMIDES
OPTICAL PURITIES

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