HETEROCYCLIC COMMUNICATIONS, vol.11, no.6, pp.471-474, 2005 (SCI-Expanded)
A synthesis of 4-(2,4,6-trimethoxyphenyl)-3,4-dihydro-2H-pyran from 2,4,6-trimethoxybenzaldehyde is reported. Radical induced cycloaddition of potassium monomethyl malonate (PMMM) to this dihydropyran has been demonstrated to give a bicyclic lactone as a single isomer. Subsequent alpha aryl substitution, ring cleavage, and rearrangement steps provided a C-aryl pyranoside derivative which represents a model for the total synthesis of blepharocalyxin E.