The Telescoped Intramolecular Michael/Olefination (TIMO) Approach to α‐Alkylidene‐γ‐butyrolactones: Synthesis of (+)‐Paeonilactone B

Abstract

Scoping out TIMO: A telescoped intramolecular Michael addition/proton transfer/Horner–Wadsworth–Emmons olefination sequence was developed to provide rapid access to α-alkylidene-γ-butyrolactones (see scheme). The method was applied to prepare a range of tetrahydrobenzofuran-2,5-diones and related systems, and it was utilized in a short synthesis of enantiomerically pure (+)-paeonilactone B.