General, regiodefined access to alpha-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory gorgonian lipid.
A variety of alpha-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.
Boukouvalas
John
J
Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada. john.boukouvalas@chm.ulaval.ca
Loach
Richard P
RP
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D001966:Bromine / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D008055:Lipids / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry*
C534374:3-bromo-2-triisopropylsilyloxyfuran; C534375:5-hydroxy-5-methyl-3-(n-hexadecyl)-2(5H)-furanone; D000893:Anti-Inflammatory Agents; D005663:Furans; D007783:Lactones; D008055:Lipids; C004511:butenolide; D008094:Lithium; D015107:4-Butyrolactone; D001966:Bromine