Asymmetric synthesis of the fully functionalized cyclodecene core of naturally occurring sesquiterpene hypocoprins A-C

Abstract

Asymmetric synthesis of fully functionalized E-cyclodecene core of naturally occurring cyclopropane containing sesquiterpenoid hypocoprins A-C was accomplished. Intramolecular HWE olefination and NHK-coupling reaction failed to provide the desired E-cyclodecene core. Finally, late stage ring closing metathesis (RCM) reaction enables the construction of fully functionalized E-cyclodecene-core of the natural products. Substrate-directed cyclopropanation and Noyori's asymmetric transfer hydrogenation are the key reactions employed to access the RCM precursor.