A unified strategy for the synthesis of the C1–C14 fragment of marinolic acids, mupirocins, pseudomonic acids and thiomarinols: total synthesis of pseudomonic acid methyl monate C

Abstract

A flexible stereoselective approach to the common C1-C14 skeleton present in natural products of the pseudomonic acid family is described. The strategy has been extended and the total synthesis of pseudomonic acid methyl monate C was achieved. The key synthetic reactions utilized include Achmatowicz rearrangement, Johnson-Claisen rearrangement, Julia-Kocienski olefination, and Horner-Wadsworth-Emmons olefination reaction.

Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates

“…A de novo approach to 2‐ C ‐branched sugar derivative 76 from the chiral furan diol 75 was reported by Sridhar and Srihari, who used Claisen rearrangement as one of the key steps 37. Compound 76 served as an excellent intermediate in the synthesis of pseudomonic acid methyl monate C ( 77 , Scheme ).…”

Synthesis of Carbon‐Branched Sugars Involving an Unprecedented 1,5‐ or 1,6‐Alkyl Transposition Reaction

“…To the best of knowledge, this is the first of its kind in the literature. The application of the developed methodology in the total synthesis of natural products and novel sugar derived scaffolds is in progress.…”

Furan Oxidation Reactions in the Total Synthesis of Natural Products

“…Further modifications of the side chains of the tetrahydropyran ring accomplished the formation of the target compound 268 (Scheme 67). 104…”