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Issue 21, 2006
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Studies in sigmatropic rearrangements of N-prenylindole derivatives – a formal enantiomerically pure synthesis of tryprostatin B

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Abstract

Rearrangement of Na-prenyl-Nb-acetyltryptamine, induced by BF3·Et2O at low temperature, leads to a 2-prenyl derivative, and thence to the tricyclic tryptamine 7 and the indoline 8. Similarly, Na-prenyl-Nb-phthaloyl-L-tryptophan methyl ester furnished the corresponding 2-prenyl derivative 16, a known advanced precursor of tryprostatin B. Density functional (B3LYP) calculations for the putative rearrangement transition state for N-prenylskatole show that prior coordination of BF3 to the indolic nitrogen changes the character of the subsequent sigmatropic pericyclic shifts from being entirely covalent to acquiring a significant degree of ionic character. The shifting prenyl group favours the endo over the exo mode of the transition state by 4.1 kcal mol−1.

Graphical abstract: Studies in sigmatropic rearrangements of N-prenylindole derivatives – a formal enantiomerically pure synthesis of tryprostatin B

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Article information


Submitted
22 May 2006
Accepted
12 Sep 2006
First published
28 Sep 2006

Org. Biomol. Chem., 2006,4, 3966-3972
Article type
Paper

Studies in sigmatropic rearrangements of N-prenylindole derivatives – a formal enantiomerically pure synthesis of tryprostatin B

A. S. P. Cardoso, M. M. B. Marques, N. Srinivasan, S. Prabhakar, A. M. Lobo and H. S. Rzepa, Org. Biomol. Chem., 2006, 4, 3966
DOI: 10.1039/B606457D

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