Modular Asymmetric Synthesis of Pochonin C

Abstract

Back to its origins: Pochonin C was synthesized in 11 steps from the four fragments shown in the scheme. This asymmetric synthesis and the conversion of pochonin C into radicicol defines the configuration at the center bearing the chlorine atom as S. Ipc=isopenocampheyl, PG=protecting group

The Hsp90 Inhibitor Radicicol Interacts with the ATP-Binding Pocket of Bacterial Sensor Kinase PhoQ

“…20,22,[40][41][42][43][44][45][46][47][48][49] For example, Proisy et al synthesized a series of macrolactones that lack the epoxide and contain different-sized macrocycle rings (13-, 14-, and 15-membered rings). 45 Crystallographic analysis demonstrates that these compounds are very similar to radicicol, only with slightly different ring sizes.…”

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

“…For example, the Lett group reported synthetic routes for a series of RALs, such as radicicol (1), monocillin I (6) [109] , LL-Z1640-2 (3), and hypothemycin (4) [110] . In 2004, a modular synthesis of pochonin C (20) was presented by the group of Winssinger [111] ; then, concise syntheses of pochonin A (18) [112] and radicicol analog A (11) [113] were reported by the same group. The Altmann group [114] reported the total syntheses of LL-Z1640-2 (3), hypothemycin (4), L-783277 (12), radicicol analog A (11), and aigialomycin D (16).…”

Resorcylic acid lactones: A pluripotent scaffold with therapeutic potential

“…Based on the therapeutic potential of HSP90 inhibition and the different biological activity of stucturally related pochonin C, we developed a synthesis to access both of the natural products [24,25]. An important criterion in our planning was the possiblity to use high throughput chemical synthesis techniques.…”