Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B

Xiao-Long Lu; Yuanyou Qiu; Baochao Yang; Haibing He; Shuanhu Gao

doi:10.1039/d0sc07089k

Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B

Chem Sci. 2021 Feb 19;12(13):4747-4752. doi: 10.1039/d0sc07089k.

Authors

Xiao-Long Lu¹, Yuanyou Qiu¹, Baochao Yang¹, Haibing He², Shuanhu Gao^{1

2}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University 3663N Zhongshan Road Shanghai 200062 China hbhe@chem.ecnu.edu.cn shgao@chem.ecnu.edu.cn.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University 3663N Zhongshan Road Shanghai 200062 China.

Abstract

The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6-7 steps using an easily accessible meso-cyclohexadienone derivative. The [6,6]-bicyclic decalin B-C ring and the all-carbon quaternary stereocenter at C-6 were prepared via a desymmetric intramolecular Michael reaction with up to 97% ee. The naphthalene diol D-E ring was constructed through a sequence of Ti(Oi-Pr)₄-promoted photoenolization/Diels-Alder, dehydration, and aromatization reactions. This asymmetric strategy provides a scalable route to prepare target molecules and their derivatives for further biological studies.