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Paper | Regular issue | Vol 27, No. 4, 1988, pp.925-932
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4438
Hetisine Derivatives Part 3. Rearrangement of 11-Acetyl-2,13-didehydrohetisine and 13-Dehydro-2,11-Diacethylhetisine

Qingping Jiang, Jan A. Glinski, Balawant S. Joshi, Joseph A. Maddry, M. Gary Newton, and S. William Pelletier*

*Department of Chemistry, Institute for Natural Products Research, The University of Georgia, Chemistry Building, Athens, Georgia 30602-2556, U.S.A.

Abstract

Heating 11-Acetyl-2,13-didehydrohetisine (1) with apueous potassium carbonate in methanol afforded a rearrangement product, C20H25NO4,mp 313-315°C. The structure of this compound has been shown to be 4 by an X-ray crystallographic study. Mild treatment of 13-dehydro-2,11-diacetylhetisine (5) with base gave 2-acetyl-13-dehydro-11-epihetisine (7). Under refluxing conditions, 5 gave the rearrangement compound 8. The structure of 8 was assigned by chromium-trioxidepyridine oxidation to give 4.