The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone
摘要:
Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.
Application of a Domino Friedel−Crafts Acylation/Alkylation Reaction to the Formal Syntheses of (±)-Taiwaniaquinol B and (±)-Dichroanone
作者:Shouchu Tang、Yanfen Xu、Jinmei He、Yongping He、Jiyue Zheng、Xinfu Pan、Xuegong She
DOI:10.1021/ol800513v
日期:2008.5.1
An efficient acid-promoted domino Friedel-Crafts (FC) acylation/alkylation reaction has been developed for the construction of the core 6,5,6-ABC tricyclic skeleton of taiwaniaquinoids. The formal total syntheses of diterpenoids (+/-)-taiwaniaquinol B and (+/-)-dichroanone based on this strategy have been achieved.