Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis

Abstract

The synthesis and application of [3.3.0]furofuranone species has received considerable attention from the scientific community. During the last twenty years, there has been a remarkable increase in publications focusing on their relevant method development as well as applications to natural product synthesis. This tutorial review discusses instructive examples to give a special emphasis on the development of new synthetic approaches and important applications to the total synthesis of natural products.

Total Synthesis of (±)-Gracilioether F

“…To our best knowledge, this intriguing molecular architecture with 1,2-dioxane has rarely been reported for synthetic approaches toward gracilioether A and its family members total synthesis. − The low natural abundance of these gracilioethers combined with their unprecedented molecular architectures and impressive biological properties prompted us to undertake their scalable total synthesis. As a continuation of our program involving the synthesis of polyketides family, herein, we present a concise approach toward the total synthesis of gracilioether F ( 1 ) through a flexible synthetic strategy which we believe may be applied to the completion of other members of these structurally intriguing gracilioether family.…”

11-Step Total Synthesis of Pallambins C and D

“…As anticipated, cyclization 4, the final ring-stitching operation of the synthesis, required invention. Although many clever strategies have been described to fashion the [3.3.0]furofuranone ring system, 16 none were suitable for the task of selectively establishing ring-D on an enol ether such as 14 . Well-trodden approaches such as epoxidation to introduce the C-11 hydroxyl group and downstream C–C bond formation failed in our hands due to chemo- and stereoselectivity issues (see SI for a summary).…”

Synthesis of anti-proliferative [3.3.0]furofuranone derivatives by lactonization and functionalization of C-glycosyl compounds

“…[13] The [3.3.0]furofuranone scaffold obtained this way is found in numerous families of biologically active natural and synthetic products explaining the continual interest nowadays in its chemistry. [15][16][17][18][19] Figure 1a shows some natural molecules with [3.3.0]furofuranone structure. (+)-Goniofufurone was isolated from Goniothalamus and the absolute configuration of natural (+)-Goniofufurone was attributed by Shing et al.…”