Journal article
Syntheses of strychnine, norfluorocurarine, dehydrodesacetylretuline, and valparicine enabled by intramolecular cycloadditions of Zincke aldehydes
Journal of organic chemistry, Vol.77(1), pp.17-46
01/06/2012
DOI: 10.1021/jo2020246
PMID: 22168233
Abstract
A full account of the development of the base-mediated intramolecular Diels-Alder cycloadditions of tryptamine-derived Zincke aldehydes is described. This important complexity-generating transformation provides the tetracyclic core of many indole monoterpene alkaloids in only three steps from commercially available starting materials and played a key role in short syntheses of norfluorocurarine (five steps), dehydrodesacetylretuline (six steps), valparicine (seven steps), and strychnine (six steps). Reasonable mechanistic possibilities for this reaction, a surprisingly facile dimerization of the products, and an unexpected cycloreversion to regenerate Zincke aldehydes under specific conditions are also discussed.
Details
- Title: Subtitle
- Syntheses of strychnine, norfluorocurarine, dehydrodesacetylretuline, and valparicine enabled by intramolecular cycloadditions of Zincke aldehydes
- Creators
- David B C Martin - Department of Chemistry, University of California, Irvine, California 92697-2025, USALucas Q NguyenChristopher D Vanderwal
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.77(1), pp.17-46
- DOI
- 10.1021/jo2020246
- PMID
- 22168233
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Language
- English
- Date published
- 01/06/2012
- Academic Unit
- Iowa Neuroscience Institute; Chemistry
- Record Identifier
- 9984065751802771
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