Total Syntheses of the Resorcylic Acid Lactones Paecilomycin F and Cochliomycin C Using an Intramolecular Loh-Type α‑Allylation Reaction for Macrolide Formation

Subjection of the resorcylic ester 16 to a Nozaki–Hiyama–Kishi reaction afforded the 12-membered lactone 17, while treatment of it under the Loh-type α-allylation conditions using indium metal gave the isomeric, 14-membered macrolide 18. Compound 18 was readily elaborated to the resorcylic acid lactone type natural products paecilomycin F and cochliomycin C.