One-Pot Synthesis of Trisubstituted Monomethylated Benzene-1,3-diols via a Michael Addition-Dieckmann Cyclization Sequence from Methyl (E)-3-Methoxy-4-methoxycarbonylbut-2-enoate Anion and Methyl Alkynoates and Its Application to the Total Synthesis of Nidulol

Adrián Covarrubias-Zúñiga; Laura San Germán-Sánchez; Luis A. Maldonado; Moisés Romero-Ortega; José G. Ávila-Zárraga

doi:10.1055/s-2005-872082

PAPER

One-Pot Synthesis of Trisubstituted Monomethylated Benzene-1,3-diols via a Michael Addition-Dieckmann Cyclization Sequence from Methyl (E)-3-Methoxy-4-methoxycarbonylbut-2-enoate Anion and Methyl Alkynoates and Its Application to the Total Synthesis of Nidulol

Adrián Covarrubias-Zúñiga*^a, Laura San Germán-Sánchez^a, Luis A. Maldonado^a, Moisés Romero-Ortega^b, José G. Ávila-Zárraga^c
^a Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F., México
e-Mail: adriancz@servidor.unam.mx;
^b Departamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Paso Tollocan, Toluca, Estado de México, México
^c Facultad de Química, Universidad Nacional Autónoma de México, Coyoacán 04510, D. F., México

Abstract

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Abstract

The reaction of methyl (E)-3-methoxy-4-methoxycarbonylbut-2-enoate (1) with a number of methyl alkynoates under appropriate conditions gave the monomethylated trisubstituted resorcinol derivatives 3 in a regiocontrolled manner, via a Michael addition-Dieckmann cyclization sequence in one pot. The resorcinol 3d, prepared in this manner, was used as the starting material for a three step, highly efficient (54% from 3d) synthesis of the bioactive fungal metabolite nidulol (4).

Keywords

resorcinol - alkynoates - Michael addition - Dieckmann cyclization - tandem reactions

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