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Paper | Regular issue | Vol 45, No. 5, 1997, pp.915-925
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7755
Coriacyclodienin and Coriacycloenin: Two New Annonaceous Acetogenins from Annona coriacea

Edna Lucia Meneses Da Silva, François Roblot, and André Cavé*

*Faculté de Pharmacie, Laboratoire de Pharmacognosie, URA 1843 CNRS (BIOCIS), 5 rue J.B. Clément 92296 Châtenay-Malabry Cedex, France

Abstract

Two new Annonaceous acetogenins, coriacyclodienin (1) and coriacycloenin (2), have been isolated from the roots of Annona coriacea Mart. (Annonaceae). 1 is the first mono-THF acetogenin which bears two double bonds in the aliphatic chain, which 2 has the same mono-THF ring and only one double bond. Both compounds (1) and (2) were oxidized and cyclized, in a one pot reaction, to give the mixtures of the four possible stereoisomer derivatives (3, 4, 5 and 6) of 1 and the two possible stereoisomer derivatives (7 and 8) of 2. The absolute stereochemistries of 1 and 2 were assigned using NMR analysis of their Mosher esters and enzymatic method.