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Synthesis 2016; 48(07): 1079-1086
DOI: 10.1055/s-0035-1561562
DOI: 10.1055/s-0035-1561562
paper
Asymmetric Synthesis of Tetrahydro-β-carboline Alkaloids Employing Ellman’s Chiral Auxiliary
Further Information
Publication History
Received: 13 November 2015
Accepted after revision: 08 January 2016
Publication Date:
05 February 2016 (online)
Abstract
A stereoselective synthesis of tetrahydro-β-carboline alkaloids has been accomplished using Ellman’s sulfinamide as a chiral source. This is the first report on the synthesis of chiral tetrahydro-β-carboline natural products using tert-butanesulfinamide through haloamide cyclization. Similarly, the synthesis of an indolizino[8,7-b]indole alkaloid, (–)-harmicine, has been achieved by means of allylation of an N-sulfinylimine, hydroboration, and SN2 substitution.
Keywords
asymmetric synthesis - chiral auxiliaries - Grignard reaction - imines - organometallic reagentsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561562.
- Supporting Information
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