Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings: a convergent synthesis of diverse benzofuran neolignans.
A convergent synthesis of diversely substituted benzofuran neolignans (8) is described employing a single p-sulfinyl group on the phenols (3) as an ambident functional group for two types of carbon-carbon bond-forming reactions: (i) the direct synthesis of the dihydrobenzofuran skeletons through an aromatic Pummerer-type reaction and (ii) the ipso-substitution of the sulfur functional group by carbon substituents through a ligand exchange reaction.
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.
S
S
Akai
N
N
Morita
K
K
Iio
Y
Y
Nakamura
Y
Y
Kita
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008094:Lithium / Q000378:metabolism; D010636:Phenols / Q000737:chemistry / Q000378:metabolism; D013441:Sulfinic Acids / Q000737:chemistry* / Q000378:metabolism
D001572:Benzofurans; D008024:Ligands; D017705:Lignans; D010636:Phenols; D013441:Sulfinic Acids; C044540:kadsurenone; D008094:Lithium