Synthesis 2008(7): 1023-1028  
DOI: 10.1055/s-2008-1066987
PAPER
© Georg Thieme Verlag Stuttgart · New York

Total Syntheses of Natural Furan Derivatives Rehmanones A, B, and C

Héctor Quiroz-Florentino, Raúl Aguilar, Blanca M. Santoyo, Francisco Díaz, Joaquín Tamariz*
Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala, 11340 México, D.F., Mexico
Fax: +52(55)57296300/46211; e-Mail: jtamariz@woodward.encb.ipn.mx;
Further Information

Publication History

Received 16 June 2007
Publication Date:
06 March 2008 (online)

Abstract

The synthesis of naturally occurring furan derivatives rehmanones­ A, B, and C is described. Diverse alternative synthetic strategies were developed for the preparation of these natural products. Conjugate addition of a furan to captodative alkene 1-acetylvinyl 4-nitrobenzoate was carried out under Lewis acid catalysis to give the corresponding adduct, which was transformed into rehmanones B and C in three and two steps, respectively. They were also prepared by condensation of acetone with the key furan-2-carb­aldehyde intermediates, which could be readily obtained from d-fructose. The bis-furan rehmanone A was not only obtained in a one-step procedure by a double condensation of acetone with 5-(methoxymethyl)furan-2-carbaldehyde, but by condensing the latter with rehmanone B in high overall yields.