Summary
Birch reduction of 9, 10-dihydroergot alkaloids (I) yields a compound to which structureII is assigned.
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References
P. A. Stadler and P.Stütz, in: The Alkaloids, vol. 15, p. 14. Ed. R. H. F. Manske, Academic Press, New York 1975.
Birch reduction of indoles has been reported to yield 2,3-and 4,7-dihydroindoles3,4.
O. Yonemitsu, P. Cerutti and B. Witkop, J. Am. Chem. Soc.,88, 3941 (1966).
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In linear proline containing peptides the N-acylproline band has been found to be reductively split by litium/methylamine8.
A. Patchornik, M. Wilchek and S. Sarid, J. Am. chem. Soc.86, 1457 (1964).
The help of A. Vigevani in interpreting the PMR spectra is gratefully acknowledged.
The isomeric structure with an exocyclic double bond can be disregarded since in the latter case the vinylic proton would be expected to give rise to a signal at a value not lower than 6.2 ppm11.
H. A. Azymauski and R. E. Yelin, in: NMR Band Handbook, p. 258. IFI/Plenum, New York 1968.
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Bernardi, L., Bosisio, G. Ergot alkaloids modified in the cyclitol moiety. Experientia 33, 704–705 (1977). https://doi.org/10.1007/BF01944138
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DOI: https://doi.org/10.1007/BF01944138