Journal article
Alkylidene Dihydropyridines As Synthetic Intermediates: Model Studies toward the Synthesis of the Bis(piperidine) Alkaloid Xestoproxamine C
Journal of organic chemistry, Vol.81(21), pp.10266-10278
11/04/2016
DOI: 10.1021/acs.joc.6b01269
PMID: 27379459
Abstract
Results of model studies demonstrating a stereoselective synthetic route to tricyclic analogues of the bis(piperidine) alkaloid xestoproxamine C are presented. Dearomatization of a tricyclic pyridine derivative to afford an alkylidene dihydropyridine (anhydrobase) intermediate followed by catalytic heterogeneous hydrogenation was used to install the correct relative stereochemistry about the bis(piperidine) ring system. Other key features of these model studies include development of an efficient ring-closing metathesis procedure to prepare macrocyclic derivatives of 3,4-disusbstituted pyridines, intramolecular cyclizations of alkylidene dihydropyridines to establish pyridine-substituted pyrrolidines and piperidines, successful homologation of pyridine-4-carboxaldehydes using formaldehyde dimethyl thioacetal monoxide (FAMSO), and application of B-alkyl Suzuki coupling to assemble substituted pyridines.
Details
- Title: Subtitle
- Alkylidene Dihydropyridines As Synthetic Intermediates: Model Studies toward the Synthesis of the Bis(piperidine) Alkaloid Xestoproxamine C
- Creators
- Ashabha I LansakaraS. V. Santhana MariappanF. Christopher Pigge
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.81(21), pp.10266-10278
- DOI
- 10.1021/acs.joc.6b01269
- PMID
- 27379459
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society
- Grant note
- DOI: 10.13039/100000165, name: Division of Chemistry, award: CHE-1265488
- Language
- English
- Date published
- 11/04/2016
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9983985863502771
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