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doi:10.1016/S0040-4039(00)83970-2    
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Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.

Rational synthesis of deuterium-labelled pyridoxal and pyridoxyl alkaloids

Gerhard Bringmann, * and Stephan Schneider

Organisch-Chemisches Institut der Universität Orléansring 23, D-4400 Münster, F.R. Germany


Received 7 October 1985. 
Available online 8 March 2001.

Abstract

A synthesis of pyridoxal is described, which avoids delicate redox reactions at the accomplished pyridoxyl system. This synthesis allows the facile preparation of highly (98%) deuterated pyridoxal 10b and of B6-derived alkaloids.

References

“Endogene Alkaloide im Menschen, 3”; 2nd communication: lit.

This work was presented in part at the 30th IUPAC congress in Manchester, UK, September 10, 1985, and at the 20. GDCh-Hauptversammlung in Heidelberg, FRG, September 16, 1985.

W. Whaley and T. Govindachari Org. React. 6 (1951), p. 151.

M.A. Collins In: The Alkaloids XXI, Academic Press, New York (1983), p. 329 A. Brossi . Abstract
G. Bringmann Naturwissenschaften 66 (1979), p. 22. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (2)

G. Bringmann and S. Schneider, Angew. Chem., submitted for publication.

H. Bader Lehrbuch der Pharmakologie und Toxikologie, Edition Medizin, Weinheim (1983).

H. Groebe Dtsch. med. Wschr. 98 (1973), p. 1313.

W.D. Lehmann and H.-R. Schulten Angew. Chem. 90 (1978), p. 233. Full Text via CrossRef

S.P. Coburn, C.C. Lin, W.E. Schaltenbrand and J.D. Mahuren J. Labelled Compd. Radiopharm. 19 (1982), p. 703 the yields for the single steps are: 42% (N-benzylation), 28% (hydrogen exchange and debenzylation), 26% (oxidation). . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (8)

H. König and W. Böll Chem.-Ztg. 100 (1976), p. 105.

T. Oshima and N. Tamiya J. Biochem. 46 (1959), p. 1675.

T. Naito, Y. Morita, S. OnishiDaiichi Seiyaku Co. and I. Tabara Chem. Abstr. 14 (1971), p. 42347 b Japan. 70 30,816 (October 6, 1970) .

W. Reppe et al.Liebigs Ann. Chem. 596 (1955), p. 115.

F. Quennehen and H. Normant Compte Rend. 228 (1949), p. 1301.

This isomerization reaction may be rationalized by elimination and regiospecific readdition of ethanol Image a reactive furo[3,4-c]pyridine.


Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 175-178
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