Synthesis of the epoxyquinol dimer RKB-3564 D: utilization of an alkoxysilanol to promote [4 + 4] dimerization.
The synthesis of the epoxyquinol dimer RKB-3564 D (3) is reported, employing an alkoxysilanol protecting group to redirect the inherently favored [4 + 2] dimerization of 2H-pyran monomers to a [4 + 4] manifold. Preliminary mechanistic studies indicate that the [4 + 4] dimerization may occur through a stepwise, ionic process.
Li
Chaomin
C
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
Porco
John A
JA
D019281:Dimerization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D006873:Hydroquinones / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D006873:Hydroquinones; C485201:RKB-3564 D; D012821:Silanes; C082343:silanol