Affiliation:
1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China
Abstract
Background:
he Wieland-Miescher ketone consists of a couple of enantiomers of 9-methyl-
Δ5(10)-octalin-1,6-dione, in which the configuration at 9-position is S- or R-type. The Robinson annulation of
2-methyl-1,3-cyclohexanedione with methyl vinyl ketone is able to afford the Wieland-Miescher ketone. As
widely used in the total synthesis, the Wieland-Miescher ketone is treated at the beginning of total synthesis,
and protocols for treating the Wieland-Miescher ketone are worthy to be addressed.
Objective:
The presented review provides the progress of the usage of Wieland-Miescher ketone for the total
synthesis, while treatments on C=C and C=O in the Wieland-Miescher ketone at the beginning of total
synthesis are exemplified herein.
Conclusion:
Modifications of the Wieland-Miescher ketone are composed of oxidation, reduction, and electrophilic
or nucleophilic addition. In addition, protection of non-conjugated C=O with glycol or protection of conjugated
C=O with ethanedithiol, and the introduction of substituents into α-position of C=C can also be used to
modify the structure of the Wieland-Miescher ketone. It is reasonably believed that many novel strategies will
be found to treat the Wieland-Miescher ketone in the future total synthesis.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry
Cited by
5 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献