Acid-catalyzed cyclization of 2,3-dibenzylidenesuccinates: synthesis of lignans (+/-)-cagayanin and (+/-)-galbulin.

Datta, P K; Yau, C; Hooper, T S; Yvon, B L; Charlton, J L

Datta, P K; Yau, C; Hooper, T S; Yvon, B L; Charlton, J L.

Affiliation

Datta PK; Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, Canada R3T 2N2.

J Org Chem ; 66(25): 8606-11, 2001 Dec 14.

Article in En | MEDLINE | ID: mdl-11735544

ABSTRACT

ABSTRACT

Acid-catalyzed cyclizations of E,E-dibenzylidenesuccinate esters have been developed as an efficient synthetic route to 1-aryl-1,2-dihydronaphthalenes. This reaction has been used in the synthesis of the naturally occurring lignans (+/-)-cagayanin and (+/-)-galbulin.

Subject(s)

Lignans/chemical synthesis; Succinates/chemistry; Tetrahydronaphthalenes/chemical synthesis; Acids; Catalysis; Cyclization; Magnetic Resonance Spectroscopy; Myristicaceae/chemistry; Photochemistry; Plants, Medicinal/chemistry

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Collection: 01-internacional Database: MEDLINE Main subject: Succinates / Tetrahydronaphthalenes / Lignans Language: En Journal: J Org Chem Year: 2001 Document type: Article

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