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Synthesis 2018; 50(17): 3493-3498
DOI: 10.1055/s-0037-1610169
DOI: 10.1055/s-0037-1610169
paper
A Convergent Total Synthesis of the Biologically Active Benzofurans Ailanthoidol, Egonol and Homoegonol from Biomass-Derived Eugenol
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 (online)
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 productsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610169.
- Supporting Information
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For syntheses of egonol and homoegonol, see:
For syntheses of ailanthoidol, see: