The power of singlet oxygen chemistry in biomimetic syntheses

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 O-1(2)-orchestrated biomimetic strategies. In these syntheses, cascade reaction sequences initiated by the reaction of O-1(2) with a furan and the ene-reaction of O-1(2) with double bonds together facilitated the swift assembly of the targeted compounds from simple precursors. We also introduce our most recent O-1(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 O-1(2), thus completing a brief survey of how O-1(2) chemistry may be fruitfully employed in the synthesis of complex secondary metabolites. (c) 2006 Elsevier Ltd. All rights reserved.