1.
J Org Chem
; 84(19): 12508-12519, 2019 10 04.
Artigo
em Inglês
| MEDLINE
| ID: mdl-31539248
RESUMO
We established a method for installing a methyl group at the ß-position of a butenolide ring. The methylated position is located at the congested ring juncture of a 5,6,5-tricyclic lactone, which is common to neurotrophic seco-prezizaane-type sesquiterpenes. The samarium(II)-mediated conjugate addition of the halomethylsilyl ethers tethered to the proximal hydroxy groups efficiently formed the desired C-C bond. Subsequent fluoride-free Tamao oxidation and Barton-McCombie deoxygenation converted the resultant cyclic silyl ether into the corresponding methyl group.