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Paper | Regular issue | Vol 85, No. 11, 2012, pp.2735-2744
Published online, 2nd October, 2012
DOI: 10.3987/COM-12-12576
Conversion of Two Eremophilane Glucosides from Pittocaulon praecox into Eremophilanolides

Amira Arciniegas, Jhon Ironzi Maldonado, Ana-L. Pérez-Castorena,* and Alfonso Romo de Vivar

*Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, D.F., Mexico

Abstract

Two eremophilanolides (3, 4), an aldehyde (6), an intramolecular addition product (7), and two water addition products (8, 9) were obtained by acid treatment of the eremophilane glucosides 10 and 11. A reaction mechanism supported by deuterium labeling is proposed for the conversion of eremophilane glycosides into eremophilanolides.