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, cilt.11, sa.6, ss.471-474, 2005 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 11 Sayı: 6
  • Basım Tarihi: 2005
  • Dergi Adı: HETEROCYCLIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.471-474
  • Çanakkale Onsekiz Mart Üniversitesi Adresli: Hayır

Özet

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.