Issue 7, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2016,7, 4725-4729

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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