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

José C. Espinoza-Hicks; Gerardo Zaragoza-Galán; David Chávez-Flores; Víctor H. Ramos-Sánchez; Joaquín Tamariz; Alejandro A. Camacho-Dávila

doi:10.1055/s-0037-1610169

Synthesis, Table of Contents

Synthesis 2018; 50(17): 3493-3498
DOI: 10.1055/s-0037-1610169

paper

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

Authors

José C. Espinoza-Hicks

^aFacultad 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

^aFacultad 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

^aFacultad 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

^aFacultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario, Campus Universitario, Apartado Postal 669, Chihuahua, 31115 Chihuahua, Mexico Email: acamach@uach.mx
Joaquín Tamariz

^bDepartamento 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
Alejandro A. Camacho-Dávila *

^aFacultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario, Campus Universitario, Apartado Postal 669, Chihuahua, 31115 Chihuahua, Mexico Email: acamach@uach.mx

Abstract

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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.

Key words

benzofurans - ailanthoidol - egonol - homoegonol - sustainable synthesis - total synthesis - natural products

Full Text

References

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Supplementary Material

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

Authors

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