The power of singlet oxygen chemistry in biomimetic syntheses

Abstract

Herein, we describe selected highlights from the successful syntheses of the litseaverticillol family of natural products and from the synthesis of the core of the prunolide molecules, using powerful 1O 2-orchestrated biomimetic strategies. In these syntheses, cascade reaction sequences initiated by the reaction of 1O 2 with a furan and the ene-reaction of 1O 2 with double bonds together facilitated the swift assembly of the targeted compounds from simple precursors. We also introduce our most recent 1O 2-facilitated synthetic strategies used in our approach to the synthesis of premnalane A. In this investigation, we explore a number of different reactivities of 1O 2, thus completing a brief survey of how 1O 2 chemistry may be fruitfully employed in the synthesis of complex secondary metabolites.