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Paper | Regular issue | Vol 27, No. 1, 1988, pp.185-193
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4335
Hetisine Derivatives, Part 1: Acetylation and Oxidation of Hetisine

Jan A. Glinski, Balawant S. Joshi, Quing Ping Jiang, 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

Acetylation of hetisine (1) under drastic conditions afforded 2-acetyl (8), 11-acetyl (9), 13-acetyl (5), 2,11-diacetyl (7), 11,13-diacetyl (2) and 2,11,13-triacetyl (6) hetisines. Sarett oxidation of the compounds (9), (5), (7) and (2) gave 11-acetyl-2,13-didehydro (11), 13-acetyl-2,11-didehydro (12), 13-dehydro-2,11-diacetyl (14) and 2-dehydro-11,13-diacetyl (10) hetisines, respectivsly. Alkaline hydrolysis of (12) and (8) gave 2,11-didehydrohetisine (13) and 2-dehydrohetisine (hetisinone) (3), respectively. Sarett oxidation of hetisine (1) afforded (13) as the major product besides 11-dahylrohetisine (15). All the compounds have been characterized by their ir, ms, 1H nmr and 13H nmr data. The location of keto groups in the hetisine derivatives (3), (10), (11), (12), (13), (14) and (15) has been confirmed by CD and ORD meaeurements.