Wieland-Gumlich aldehyde

This article will address Wieland-Gumlich aldehyde, a topic that has gained relevance in recent years due to its impact in various contexts. From the Wieland-Gumlich aldehyde perspective, its importance and impact on _var2 will be analyzed, as well as its influence on _var3. Throughout this document, different approaches and points of view on Wieland-Gumlich aldehyde will be presented, in order to provide a comprehensive and updated vision of this topic. Likewise, concrete examples and case studies will be presented that will practically illustrate the relevance of Wieland-Gumlich aldehyde today. With a multidisciplinary approach, the aim is to offer a holistic vision of Wieland-Gumlich aldehyde, allowing readers to understand its scope and applications in various areas.

Wieland-Gumlich aldehyde
Names
IUPAC name
(1S,9S,10R,11R,12E,17S)-12-(2-hydroxyethylidene)-8,14-diazapentacyclooctadeca-2,4,6-triene-10-carbaldehyde
Other names
Caracurine VII, Deacetyldiaboline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C19H22N2O2/c22-8-5-12-10-21-7-6-19-15-3-1-2-4-16(15)20-18(19)14(11-23)13(12)9-17(19)21/h1-5,11,13-14,17-18,20,22H,6-10H2/b12-5-/t13-,14+,17-,18-,19+/m0/s1
    Key: ZOMKIDXZHXWPCN-DYAJAIQSSA-N
  • InChI=1/C19H22N2O2/c22-8-5-12-10-21-7-6-19-15-3-1-2-4-16(15)20-18(19)14(11-23)13(12)9-17(19)21/h1-5,11,13-14,17-18,20,22H,6-10H2/b12-5-/t13-,14+,17-,18-,19+/m0/s1
    Key: ZOMKIDXZHXWPCN-DYAJAIQSBC
  • C1CN2C/C(=C/CO)/3C214(3C=O)NC5=CC=CC=C45
Properties
C19H22N2O2
Molar mass 310.397 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

The so-called Wieland-Gumlich aldehyde (6) is an indoline derived by chemical degradation from strychnine. This compound is of some commercial interest as a chemical intermediate. It was first synthesized in 4 steps from strychnine (1) by Walter Gumlich and Koozoo Kaziro working in the laboratory of Heinrich Wieland. This degradation study was part of an attempt to elucidate the chemical structure of strychnine.

This degradation takes place through conversion of strychnine to the oxime 2 using amyl nitrite, Beckmann fragmentation of 2 to the carbamic acid 3 by use of thionyl chloride, decarboxylation of 3 to nitrile 4, and nucleophilic displacement of cyanide by barium hydroxide to give hemiacetal 5, which is in equilibrium with the Wieland-Gumlich aldehyde (6).

The Wieland-Gumlich aldehyde synthesis

The Wieland-Gumlich aldehyde reverts to strychnine in a single reaction using malonic acid, acetic anhydride and sodium acetate in acetic acid.

The Wieland-Gumlich aldehyde has been used in the industrial synthesis of alcuronium chloride (Alloferin) via dimerization.

References

  1. ^ Chambers, Michael. "ChemIDplus - 466-85-3 - UFUDXCDPABDFHK-SRCYXDNASA-N - Wieland-gumlich aldehyde - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
  2. ^ Wieland, H.; Gumlich, W. (1932) Über einige neue Reaktionen der Strychnos - Alkaloide. XI Justus Liebigs Annalen der Chemie 494(1):191-200. (original report of fragmentation of the strychnine lactam ring)
  3. ^ Wieland H.; Kaziro, K. (1933) Abbauversuche vom Isonitroso-strychnin aus. Über Strychnos-Alkaloide. XIII Justus Liebigs Annalen der Chemie 506(1):60–76. (definitive characterization of the Wieland-Gumlich aldehyde)
  4. ^ Witkop B. (1992) Remembering Heinrich Wieland (1877-1957) Portrait of an Organic Chemist and Founder of Modern Biochemistry Med. Res. Rev. 12(3):195-274. (Witkop notes that "Wieland and Kaziro studied the Beckmann rearrangement of this oxime and the loss of hydrogen cyanide to yield an aldehyde, that should correctly be called Wieland-Kaziro aldehyde, but became known and accepted as Wieland-Gumlich aldehyde...")
  5. ^ F. A. L. Anet, R. Robinson, Chem. Ind. (London) 1953, 245.
  6. ^ Alkaloids: Nature's Curse or Blessing? Manfred Hesse. Wiley, 2002. See pp. 230-232. ISBN 978-3-90639-024-6
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