Orbital - Vol. 12 No. 2 - April-June 2020
SHORT COMMUNICATIONS

A Straightforward Method for Synthesizing Bioactive Resorcinolic Lipid Analogues

Denilson Silva dos Santos
Universidade Federal de Mato Grosso do Sul
Alisson Meza
Centro Universitário Anhanguera de Campo Grande
Roberto da Silva Gomes
Department of Pharmaceutical Sciences, North Dakota State University, Fargo
Dênis Pires de Lima
Universidade Federal de Mato Grosso do Sul
Adilson Beatriz
Universidade Federal de Mato Grosso do Sul
Published June 29, 2020
Keywords
  • resorcinolic lipids,
  • cytosporones,
  • phomopsin C,
  • cladosporin
How to Cite
(1)
dos Santos, D. S.; Meza, A.; Gomes, R. da S.; de Lima, D. P.; Beatriz, A. A Straightforward Method for Synthesizing Bioactive Resorcinolic Lipid Analogues. Orbital: Electron. J. Chem. 2020, 12, 100-104.

Abstract

Resorcinolic lipids, a class of bioactive amphiphilic molecules found widely in nature, hold potential for a variety of biological and industrial applications. This report describes the synthesis of three bioactive structural analogues of resorcinolic lipids, obtained by subjecting ethyl (E)-2-undecenoate and ethyl acetoacetate to a Michael reaction in the presence of sodium ethoxide to generate a Michael adduct, followed by cyclization in the reaction medium. Ethyl 2-octyl-4,6-dioxocyclohexanecarboxylate (7) was thus produced with a 60% yield. To perform an aromatization step, 7 was subsequently treated with I2 in methanol under reflux, producing a combined 80% yield of 2,4-dimethoxy-6-octyl-ethyl benzoate (1) and 2-hydroxy-4-methoxy-6-octyl-ethyl benzoate (2) at a 7:3 ratio, respectively. 2-Hydroxy-4-methoxy-6-octyl-benzoic acid was obtained with a 60% yield by treating 1 with BBr3/CHCl3. The structures of the synthesized compounds and intermediates were elucidated by 1H and 13C NMR spectroscopy, employing two-dimensional techniques (HSQC and HMBC).

DOI: http://dx.doi.org/10.17807/orbital.v12i2.237