First synthesis of (±)-myristicyclin A

Abstract

The first synthesis of myristicyclin A, which was isolated from the Papua New Guinean plant Horsfieldia spicata, is described. The synthesis features acid-mediated hydroarylation reaction to form a dihydrocoumarin moiety, construction of the 2,8-dioxabicyclo[3.3.1]nonane skeleton under acidic conditions, and regioselective Friedel-Crafts acylation at a later stage.

Recent advances in the synthesis of natural products containing the phloroglucinol motif

“…252 They contain an interesting 2,8-dioxabicyclo[3.3.1]nonane scaffold and possess antimalarial activity against Plasmodium falciparum . Three years after the first reported eight-step synthesis of myristicyclin A, 253 the Gharpure group disclosed an one-pot syntheses of myristicyclins A and B with excellent atom economy (Scheme 69). 254 In their work, treatment of 395 with camphorsulfonic acid (CSA) and trimethyl orthoformate generated the o -quinine methide intermediate in situ , followed by concomitant Diels–Alder cycloaddition with 396 to furnish 397 .…”