Synthesis of 3-azabicyclo[3.3.0]octane framework and a novel tricyclicaminoether

Kaniskan H., Dogan O.

SYNTHETIC COMMUNICATIONS, vol.33, no.21, pp.3833-3841, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 21
  • Publication Date: 2003
  • Doi Number: 10.1081/scc-120025195
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3833-3841
  • Middle East Technical University Affiliated: Yes

Abstract

The efficient synthesis of 3-azabicyclo[3.3.0]octane derivative 1 and a novel tricyclicaminoether 11 has been achieved in seven steps using commercially available starting materials and commonly used reagents. The key steps are the intramolecular ring opening of epoxide 7 providing tricyclic aminoalcohol 3 and Baeyer-Villiger oxidation of ketone 8 providing the corresponding lactone 2. Both reactions proceeded regiospecifically.