| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5213579 | Tetrahedron | 2016 | 7 Pages |
Abstract
A general route to several styryl-lactone frameworks is presented. Starting from a known enol ether, stereoselective epoxidation and methanolysis yields a series of three distinct hydroxyacetals, each further functionalized by etherification with an allylic vinylsilane fragment. A highly efficient Lewis acid-promoted intramolecular annulation at the tethered oxocarbenium allows direct entry to cis-fused bicyclic ether cores. Further manipulation delivers a variety of additional styryl-lactone motifs and analogs; for example, simple allylic oxidation yields 3-deoxyisoaltholactone, in just five steps overall.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Stephen Philip Fearnley, Pedro Lory,