Asymmetric synthesis of a functionalized tricyclo[6.2.0.02,6]decane ring system present in kelsoene and poduran

Abstract

Listen

Translate article

Synthesis of a functionalized tricyclo[6.2.0.02,6]decane derivative in enantiomerically pure form, the core structure present in the natural products kelsoene and poduran, is described. The key steps involve a stereocontrolled copper (I)-catalyzed intramolecular [2 + 2] photocycloaddition of a 1, 6-diene prepared from D-mannitol to form a substituted bicyclo[3.2.0]heptane derivative and a ring closing olefin metathesis involving the vicinal substituents on the five-membered ring of the bicyclo[3.2.0]heptane derivative. An asymmetric synthesis of a functionalized tricyclo[6.2.0.02,6]decane derivative has been described. The key step involves an intramolecular Cu (I)-catalyzed [2 + 2] photocycloaddition of a 1,6-diene derived from D-mannitol to provide a bicyclo[3.2.0]heptane derivative. Annulation of a five-membered ring on to the five-membered ring of this derivative using RCM provided the title compound.