Intramolecular Involvement of an Oxygen-containing Nucleophilic Group in Epoxy Ring Opening

Abstract

The objective of the review is analysis of reactions occurring in epoxy compounds with additional oxygen-containing group (carbonyl, epoxy ring or alcohol group) attached to its skeleton, and the description of the biological aspects of the reactions. The mechanisms of the reactions, the stereo-and regioselectivity of transformations are discussed.

Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes

“…Furthermore, attempts to open the epoxide by elimination were uniformly unsuccessful. Surprisingly, treating 54 with LDA did not create a C2–C3 alkene; instead, intramolecular displacement of the epoxide by a lactone enolate occurred preferentially at the C4 position, affording 55 in good yield . The remarkable cyclopropanated structure was confirmed by single crystal X-ray analysis.…”

Three‐Membered Heterocycles. Structure and Reactivity

“…Other oxygen-containing heterocycles with varying degrees of structural complexity are conveniently prepared by the intramolecular ring-opening of epoxides [592]. An illustrative example is found with the titanium-promoted cyclization of the highly oxygenated bicyclic epoxide 537 to give the spiroketal 538 with retention of configuration [593].…”

Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans

“…1 Many methods have been developed for the synthesis of THPs as described in previous informative reviews. [2][3][4][5][6] Common approaches include Prins cyclisations, hetero-Diels-Alder reactions and ring closing metatheses (Fig. 2).…”