Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: short syntheses of stemofuran a and eupomatenoid 6.
A new and efficient synthesis of 2-arylbenzofurans has been achieved via a route involving acylation and subsequent [3,3]-sigmatropic rearrangement of oxime ethers. Its synthetic utility is demonstrated by a short synthesis of stemofuran A and eupomatenoid 6 in which no procedure for protection of the phenolic hydroxyl groups is needed. [reaction--see text]
Miyata
Okiko
O
Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Takeda
Norihiko
N
Naito
Takeaki
T
D000215:Acylation; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004986:Ether / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry
D001572:Benzofurans; D010091:Oximes; D010636:Phenols; C489063:stemofuran A; D004986:Ether; C452812:eupomatenoid 6