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Issue 7, 2016
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Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure

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Abstract

A divergent enantioselective approach to hapalindole-type alkaloids is described. The route features a ruthenium-catalyzed asymmetric hydrogenation of a ketone via DKR to construct the chiral trans-1-indolyl-2-isopropenylcyclohexane skeleton and a switchable sequence of methylation and acetylation/aldol reaction to access a chiral quaternary stereocenter. (+)-Hapalindole Q (1, 13 steps, 5.9% overall yield), (−)-12-epi-hapalindole Q isonitrile (2, 15 steps, 5.5% overall yield), (−)-hapalindole D (3, 14 steps, 2.3% overall yield), and (+)-12-epi-fischerindole U isothiocyanate (4, 14 steps, 3.0% overall yield) were synthesized in 13–15 steps from a commercially available material to demonstrate the application of this approach.

Graphical abstract: Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure

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Article information


Submitted
15 Feb 2016
Accepted
12 Apr 2016
First published
12 Apr 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 4725-4729
Article type
Edge Article

Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure

Y. Liu, L. Cheng, H. Yue, W. Che, J. Xie and Q. Zhou, Chem. Sci., 2016, 7, 4725
DOI: 10.1039/C6SC00686H

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