Synthesis 2018; 50(17): 3493-3498
DOI: 10.1055/s-0037-1610169
paper
© Georg Thieme Verlag Stuttgart · New York

A Convergent Total Synthesis of the Biologically Active Benzo­furans Ailanthoidol, Egonol and Homoegonol from Biomass-Derived­ Eugenol

José C. Espinoza-Hicks
a  Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario, Campus Universitario, Apartado Postal 669, Chihuahua, 31115 Chihuahua, Mexico   Email: acamach@uach.mx
,
Gerardo Zaragoza-Galán
a  Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario, Campus Universitario, Apartado Postal 669, Chihuahua, 31115 Chihuahua, Mexico   Email: acamach@uach.mx
,
David Chávez-Flores
a  Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario, Campus Universitario, Apartado Postal 669, Chihuahua, 31115 Chihuahua, Mexico   Email: acamach@uach.mx
,
Víctor H. Ramos-Sánchez
a  Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario, Campus Universitario, Apartado Postal 669, Chihuahua, 31115 Chihuahua, Mexico   Email: acamach@uach.mx
,
Joaquín Tamariz
b  Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. de Carpio y Plan de Ayala S/N, 11340 Ciudad de Mexico, Mexico
,
a  Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario, Campus Universitario, Apartado Postal 669, Chihuahua, 31115 Chihuahua, Mexico   Email: acamach@uach.mx
› Author Affiliations
We express our gratitude to the Consejo Nacional de Ciencia y Tecnología (CONACYT) (Mexico) for a grant to purchase the NMR instrument (INFR-2014-01-226114). J.T. gratefully acknowledges SIP-IPN (grants 20170791 and 20180198) and CONACYT (grant 178319) for financial support. J.T. is a fellow of the EDI-IPN and COFAA-IPN programs.
Further Information

Publication History

Received: 06 April 2018

Accepted after revision: 03 May 2018

Publication Date:
28 June 2018 (eFirst)

Abstract

An efficient, general synthetic protocol for the synthesis of the biologically active benzofurans ailanthoidol, egonol and homoegonol was developed. The key starting material, eugenol, is a naturally occurring and abundant precursor. The protocol, involving sequential acylation and intramolecular Wittig reaction, provides a convenient method for building the benzofuran moiety in good yield.

Supporting Information

 
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