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Communication | Special issue | Vol 13, No. 1, 1979, pp.277-280
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0277
The Mechanism of the Garryfoline-Cuauchichicine Rearrangement

S. William Pelletier,* Haridutt K. Desai, and Naresh V. Mody

*Institute for Natural Products Research, The Department of Chemistry, University of Georgia, Athens, Georagia 30602, U.S.A.

Abstract

The acid-catalyzed rearrangement of garryfoline to cuauchichicine has been studied by deuterium labeling and 13C NMR spectroscopy to establish its mechanism. Treatment of isogarryfoline with 10% DCI in D2O yielded a product with a C(16αD) - βCH2D group, a fact which demonstrates that the rearrangement involves enol formation followed by exo-protonation.