Total synthesis of twelve membered resorcyclic acid lactones, (R)-penicimenolide A, (R)-resorcyclide and (R)-dihydroresorcyclide

Resorcyclic Acid Lactones or RALs are a class of fungal secondary polyketides isolated from a variety of fungal strains like Lasiodiplodia theobromae, Penicillium sp., Syncephalastrum racemosum etc. This class of macrocyclic lactones are found to exhibit a broad spectrum of biological activities and are of significant synthetic importance. Herein, we report the first total synthesis of (R)-penicimenolide A, twelve membered RAL (RAL12) isolated from Penicillium sp. (NO. SYP-F-7919). Besides, we also report the total synthesis of two other members, namely, (R)-trans-resorcyclide and (R)-dihydroresorcyclide. In the course of synthesis, we have utilized ring closing metathesis (RCM) as the key step in constructing the core macrolactone scaffold. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

Resorcyclic Acid Lactones (RALs) are fungal secondary polyketides with broad biological activities and synthetic importance. The total synthesis of (R)-penicimenolide A, (R)-trans-resorcyclide, and (R)-dihydroresorcyclide was reported, utilizing ring closing metathesis as a key step in constructing the core macrolactone scaffold.