Exploration of ring rearrangement metathesis reaction: A general and flexible approach for the rapid construction [5,n]-Fused bicyclic systems en route to linear triquinanes

Abstract

Structurally diverse [5,n] bicyclic systems with cis ring junction stereochemistry were accessed readily through RRM (ring rearrangement metathesis) reaction of properly functionalized [2.2.1]norbornene skeletons. Several bicyclic enones, ketones, alcohols, and ethers acted as the substrates and yielded the respective linearly fused [5,n] bicyclic systems stereoselectively after the RRM reaction. Such [5,5]bicyclic enone scaffolds were then synthetically manipulated to core structural analogue of naturally occurring liner triquinane hirsutene having cis-syn-cis stereochemistry.