Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B. Issue 13 (25th February 2021)

• Record Type: Journal Article
• Authors: Lu, Xiao-Long; Qiu, Yuanyou; Yang, Baochao; He, Haibing; Gao, Shuanhu
• Is Part Of: Chemical science. Volume 12:Issue 13(2021)
• Page Start: 4747
• Page End: 4752
• Publication Date: 2021-02-25
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc07089k
• Languages: English
• ISSNs: 2041-6520

Abstract

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. 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.