Acid-catalyzed cyclization of 2,3-dibenzylidenesuccinates: synthesis of lignans (+/-)-cagayanin and (+/-)-galbulin.
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.
Datta
P K
PK
Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, Canada R3T 2N2.
Yau
C
C
Hooper
T S
TS
Yvon
B L
BL
Charlton
J L
JL
D000143:Acids; D002384:Catalysis; D003500:Cyclization; D017705:Lignans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D026324:Myristicaceae / Q000737:chemistry; D010777:Photochemistry; D010946:Plants, Medicinal / Q000737:chemistry; D013386:Succinates / Q000737:chemistry*; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis*
D000143:Acids; D017705:Lignans; D013386:Succinates; D013764:Tetrahydronaphthalenes; C443727:cagayanin; C412027:galbulin