Efficient synthesis of butenolide-medium ring ether hybrids by a [3 + 2] cyclization-ring-closing metathesis strategy.
A new strategy for the synthesis of bicyclic gamma-alkylidenebutenolides, butenolide-medium ring ether hybrids, is reported which involves Me(3)SiOTf-catalyzed cyclization of 1, 3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride, Mitsunobu reaction, and subsequent ring-closing metathesis.
Langer
P
P
Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany. planger@uni-goettingen.de
Eckardt
T
T
Stoll
M
M
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D001685:Biological Factors / Q000138:chemical synthesis / Q000302:isolation & purification; D002070:Butadienes / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*
D001685:Biological Factors; D002070:Butadienes; D004988:Ethers, Cyclic; D005663:Furans; C004511:butenolide; D015107:4-Butyrolactone