Stereoselective synthesis of the epicoccin core.
A short, convergent, and asymmetric synthesis of the epicoccin core was achieved using a phosphite-promoted one-step condensation of a complex proline-type amino acid. Key features of the assembly of this amino acid were a double-bond isomerization/vinylation/ring-closing metathesis strategy as well as an efficient, highly diastereoselective [2 + 2] cycloaddition of a ketene to an enecarbamate, derived from L-pyroglutamic acid.
Gross
Ulrike
U
Institute of Organic Chemistry, Karlsruhe Institute of Technology, Germany.
Nieger
Martin
M
Bräse
Stefan
S
D053138:Cyclohexenes / Q000737:chemistry; D007536:Isomerism; D007783:Lactones / Q000737:chemistry; D010879:Piperazines / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D053138:Cyclohexenes; D007783:Lactones; D010879:Piperazines; C052568:cyclohexene