Acid-catalyzed rearrangement of pyran derivatives. An approach to the stereoselective synthesis of 1,3-diol derivatives

✍ Scribed by Philip DeShong; David M Simpson; Ming-Teh Lin

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 274 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99149-4

✦ Synopsis

Peracid oxidation and HF-catalyzed treatment of furfuryl alcohol derivatives affords lactone products arising from a highly stereoselective rearrangement process. The lactones serve as precursors of highly functionahzed anti-1,3-dial derivatives.

During the studies directed toward the total synthesis of thandamycin ~1 and the pheromone of the male swift moth Hepiulus hecta L2 it was demonstrated that the 2.6dioxabicyclo[3.3. llnonane ring system of