We have investigated 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 asymmetric Diels-Alder reaction, we have launched a program inventing a new route that allows an efficient asymmetric synthesis of cyanthiwigin F and platensimycin. The key transformations include C3-selective Sonogashira coupling of 3,5-dibromo-2-pyrone, chemo-selective hydrogenation and intramolecular Diels-Alder cyclization. Presented herein is our recent progress toward total synthesis of (-)-cyanthiwigin F and (-)-platensimycin.

Progress toward total synthesis of (-)-platensimycin and (-)-cyanthiwigin F by internal H-bonding mediated intramolecular Diels-Alder reaction

2019 Fall National Meeting

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