Rapid Construction of the Scaffold of Quorumolide A Enabled by a Tandem ROM/RCM Strategy and a Tandem Oxidative Cyclization Strategy

Abstract

A synthetically challenging framework in the plant-derived cembranoid quorumolide A was established in a seven-step sequence featuring a ring-opening/-closing metathesis cascade reaction to construct the fused butenolide ring and the 14-membered macroring in a single step. The utilization of a tandem oxidative cyclization strategy is the key to build the tetrahydro-2H-pyran moiety.

Euphorbiaditerpenoids: isolation, structure, bioactivity, biosynthesis, and synthesis (2013–2021)

“…41 In 2019, Chen and co-workers developed a concise and asymmetric synthetic route to construct the unique core of quorumolide A in a seven-step sequence (Scheme 16). 377 The strategy used a ring opening/closing metathesis (ROM/RCM) cascade reaction and a tandem oxidative cyclization as the key steps, constructing the fused butenolide ring and the 14-membered macroring in a single step. The synthesis commenced with the asymmetric Mukaiyama-type aldol reaction between the easily prepared S20 and S21 to deliver S22 .…”