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Synthesis 2005(14): 2293-2296  
DOI: 10.1055/s-2005-872082
PAPER
© Georg Thieme Verlag Stuttgart · New York

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-Sáncheza, Luis A. Maldonadoa, Moisés Romero-Ortegab, José G. Ávila-Zárragac
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
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Publication History

Received 16 August 2004
Publication Date:
20 July 2005 (online)

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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