Stereospecific syntheses of the lignans: 2-S-(3,4-dimethoxybenzyl)-3-R-(3,4,5-trimethoxybenzyl) butyrolactone, and its positional isomeric lactone

Article abstract of DOI:10.1080/00397919308009859

A short, versatile and stereospecific synthesis of two lignans 1 and 2, was achieved in 40% overall yield. Our strategy was based in the use of amino acids as chiral and readily available starting materials. Stereocontrolled transformation of amino acids to chiral organic phosphonates gave the key intermediate of the synthetic sequence. A Horner-Wadsworth-Emmons (HWE) reaction followed by selective reduction and stereospecific hydrogenation in the last step resulted in the title compounds with the desired absolute stereochemistry.

Full text of DOI:10.1080/00397919308009859

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Synthetic Communications: An
International Journal for Rapid
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Organic Chemistry
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Stereospecific Syntheses
of the Lignans: 2-S-(3,4-
Dimethoxybenzyl)-3-R-
(3,4,5-trimethoxybenzyl)
Butyrolactone, and Its
Positional Isomeric Lactone
Alírica Suárez a , Francisco López a & Reinaldo S.
Compagnone a
a Centro de Química Orgánica, Escuela de Química,
Facultad de Ciencias, Universidad Central de
Venezuela, Apartado, 47102, Caracas, Venezuela
Version of record first published: 16 Feb 2007.
To cite this article: Alírica Suárez, Francisco López & Reinaldo S. Compagnone (1993):
Stereospecific Syntheses of the Lignans: 2-S-(3,4-Dimethoxybenzyl)-3-R-(3,4,5-
trimethoxybenzyl) Butyrolactone, and Its Positional Isomeric Lactone, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 23:14, 1991-2001
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