A concise asymmetric synthesis of (−)-trans-aerangis lactone

Abstract

A concise stereoselective approach to functionalized δ-lactone skeleton from monosilylated ethylene glycol as a starting material and its application to the asymmetric total synthesis of (−)-trans-aerangis lactone have been demonstrated. The synthesis utilizes the organocatalyzed MacMillan’s cross aldol reaction as a key step.

Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones

“…Subsequent DAIB/TEMPO oxidation gave stable aldehyde 21. To our delight, olefinations of 21 with both 15 30 and 16 31 were successful and afforded compounds 22 and 23 in acceptable yields. Regeneration of the lactone moiety was first attempted with Jones reagent; however, only decomposition products were observed.…”