Studies toward total synthesis of (-)-platensimycin by internal H-bonding mediated intramolecular Diels-Alder reaction

Abstract

We have studied 3,5-dibromo-2-pyrone towards target-oriented synthesis, utilizing its peculiar reactivity as a neutral diene and the selective maneuverability of the two bromine groups. Such efforts have resulted in successful syntheses of an array of biologically important natural products.

Inspired by our recent success on internal hydrogen bonding mediated intramolecular Diels-Alder (IMDA) reaction, we have launched a program inventing a new route that allows an efficient asymmetric synthesis of (-)-platensimycin. The key transformations include C3 selective Sonogashira coupling of 3,5-dibromo-2-pyrone, chemoselective hydrogenation and π-facial selective IMDA cyclization. Presented herein are the results so far and future direction toward total synthesis of (-)-platensimycin.