Total synthesis of seco-lateriflorone

Abstract

A convergent strategy toward the synthesis of lateriflorone ( 5 ) is described. Our approach is based on biosynthetic considerations and draws on a sequence of prenylation, oxygenation and Claisen reactions for the construction of chromenequinone 6 , and a tandem Claisen/Diels–Alder reaction cascade for the synthesis of caged tricycle 7 . Union of fragments 6 and 7 led to the synthesis of seco-lateriflorone ( 49 ).