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Studies on the synthesis of Medusaside-A

Grant number: 08/04300-0
Support Opportunities:Scholarships in Brazil - Scientific Initiation
Effective date (Start): September 01, 2008
Effective date (End): January 31, 2010
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Acordo de Cooperação: NSF - American Universities (Chemistry)
Principal Investigator:Fernando Antonio Santos Coelho
Grantee:Renan Lourenço Joviliano
Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil


This undergraduate scientific project intend to establishing a synthetic sequence for the preparation of racemic Medusaside-A. Recently, this lignan has been isolated, as main constituent, from a plant of the Astereaceae family (Saussurea meduca, Maxim). This plant is currently used in the tradicional chinese medicine to the treament and healing of reumathroid arthrytes, dysmenorreia and gynopathies. Despite its pharmacological relevance, up to now there is not a report on the total synthesis of this lignan available in literature.In this undegraduate scientific project we intend to use a synthetic sequence previously establisehd in our laboratory for preparing Medusaside-A. The strategy is based on a Michael addition of cyanate over a Morita-Baylis-Hillman adduct. The cyanated adduct will be tranformed into a lactone, that will be used as substrate for an alkylation step. The reduction of the alkylated lactone will provide the required lignan in its racemic form. (AU)

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