The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H)-furanone (>99% ee) was used for the formal total synthesis of (+)-dubiusamine A (1).
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry