Abstract
The direct oxidative cyclization of 1,5-dienes is a valuable synthetic method for the (dia)stereoselective preparation of substituted tetrahydrofurans. Closely related reactions start from 5,6-dihydroxy or 5-hydroxyalkenes to generate similar products in a mechanistically analogous manner. After a brief overview on the history of this group of transformations and a survey on mechanistic and stereochemical aspects, this review article provides a summary on applications in natural product synthesis. Moreover, current limitations and future directions in this area of chemistry are discussed.
Highlights
Scope of this articleAfter a concise introduction on the history and mechanistic aspects of the title reaction, the primary aim of the present review article is to summarize all relevant applications in natural product synthesis
After a brief overview on the history of this group of transformations and a survey on mechanistic and stereochemical aspects, this review article provides a summary on applications in natural product synthesis
Previous review articles concerning oxidative diene cyclization chemistry can be considered in complement [4,5,6]
Summary
After a concise introduction on the history and mechanistic aspects of the title reaction, the primary aim of the present review article is to summarize all relevant applications in natural product synthesis. Methodology driven investigations as well as mechanistic studies are not the main focus of this review but may be mentioned in the introductory section. Syntheses of fragments of natural products applying an oxidative cyclization protocol [1,2] and sequential epoxidation/cyclization procedures [3] are not in the scope of this article and are not covered. Previous review articles concerning oxidative diene cyclization chemistry can be considered in complement [4,5,6]. Oxidative cyclization – Historical background In 1924 Kötz and Steche reported on an investigation of the constitution of the monoterpene geraniol (1, R = H) [7].
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