Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A?

Organic Chemistry Frontiers Pub Date: 2017-08-15 DOI: 10.1039/C7QO00550D

Abstract

A tandem radical cyclization reaction towards the 6/6/5 fused tricyclic skeleton, which exists in numerous natural products, was developed in modest to good yields. In this transformation, two C–C bonds and two rings were formed successively via a tandem 5-exo-trig/6-endo-trig cyclization reaction. 5-epi-7-deoxy-Isoabietenin A was also synthesized efficiently via this strategy.

Graphical abstract: Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A
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