Naphthalene analogues of lignans.
The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained from the 1,3-dithiane of 1-naphthaldehyde. In this series, polycyclic naphthalene lignan analogues were isolated after deprotection and/or desulfurization reactions. The cyclizations produced in this process are due to the proximity between the 3,4,5-trimethoxyphenyl moiety and the reacting C-2 of the 1,3-dithiane ring.
Madrigal
Blanca
B
Laboratorio de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, Campus Miguel de Unamuno, E-37007 Salamanca, Spain.
Puebla
Pilar
P
Peláez
Rafael
R
Caballero
Esther
E
Medarde
Manuel
M
D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D004951:Esterification; D007202:Indicators and Reagents; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011034:Podophyllotoxin / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002227:Carbazoles; D007202:Indicators and Reagents; D017705:Lignans; D009281:Naphthalenes; C452999:thuriferic acid; C031721:naphthalene; D011034:Podophyllotoxin