A relay ring-opening/double ring-closing metathesis strategy for the bicyclic macrolide-butenolide core structures

Abstract

A concise strategy has been developed for the synthesis of the bicyclic macrolide-butenolide core structures of various natural products with the macrolide ring size ranging from 12- to 16-membered. The bicyclic structure was easily assembled using the relay ring-opening/double ring-closing metathesis strategy. An efficient synthesis of (±)-desmethyl manshurolide has been achieved as an application of this strategy.