Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans.
The first total syntheses of the racemates of naturally occurring macrophyllin-type bicyclo[3.2.1]octanoid neolignans, kadsurenin C 3 and kadsurenin L 4, were accomplished starting from vanillin and resorcinol. The acid-catalyzed rearrangement of hydrobenzofuranoid neolignans into bicyclo[3.2.1]octanoid neolignans was used as the key step.
Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Mingyi
M
Wang
Anxin
A
Wu
Xinfu
X
Pan
Hongfang
H
Yang
D001547:Benzaldehydes / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D034242:Cyclooctanes; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D017705:Lignans / Q000138:chemical synthesis*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012118:Resorcinols / Q000737:chemistry; D013237:Stereoisomerism
D001547:Benzaldehydes; D001643:Bridged Bicyclo Compounds; D034242:Cyclooctanes; D004365:Drugs, Chinese Herbal; D017705:Lignans; D012118:Resorcinols; C470614:kadsurenin C; C082848:kadsurenin L; C100058:vanillin; C031389:resorcinol