Total Synthesis of Atrachinenins A and B

Abstract

Inspired by a new biosynthetic hypothesis, we report a biomimetic total synthesis of atrachinenins A and B that explains their racemic nature. The synthesis exploits an intermolecular Diels–Alder reaction between a quinone meroterpenoid and E-β-ocimene, followed by intramolecular (3 + 2) cycloaddition and a late-stage aerobic oxidation. Divergent transformations of a simple model system gave several complex polycyclic scaffolds, while also suggesting a structure revision for atrachinenin C.

Synthesis and Biological Evaluation of Cleistocaltone A, an Inhibitor of Respiratory Syncytial Virus (RSV)

“…These strategies elegantly mimic the pathways found in nature. [17][18][19] By harnessing the innat e reactivity of molecules, biomimetic syntheses often minimize the need for protection groups, resulting in greater efficienc y and sustainability. 20 Mirroring the proposed biosynthetic pathway, we envision e d an IMDA as the pivotal step for constructing the 10-membe r e d macrocycle of 8.…”

Synthesis and biological evaluation of cleistocaltone A, an inhibitor of respiratory syncytial virus (RSV)

“…These strategies elegantly mimic the pathways found in nature. [17][18][19] By harnessing the innate reactivity of molecules, biomimetic syntheses oen minimize the need for protection groups, resulting in greater efficiency and sustainability. 20 Mirroring the proposed biosynthetic pathway, we envisioned an IMDA as the pivotal step for constructing the 10-membered macrocycle of 8.…”

“…These strategies elegantly mimic the pathways found in nature. 17–19 By harnessing the innate reactivity of molecules, biomimetic syntheses often minimize the need for protection groups, resulting in greater efficiency and sustainability. 20…”