Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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.


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.