Synthesis and ring cleavage of a sterically hindered tetrarydro-4H-furo [2,3-b]pyran-2-one. A model for the total synthesis of blepharocalyxin E

Cakir S., MEAD K.

HETEROCYCLIC COMMUNICATIONS, vol.11, no.6, pp.471-474, 2005 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 11 Issue: 6
  • Publication Date: 2005
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.471-474
  • Çanakkale Onsekiz Mart University Affiliated: No


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.