Review
Version 1
Preserved in Portico This version is not peer-reviewed
Progress in Lewis Acid Template-Mediated Diels-Alder Reaction
Version 1
: Received: 3 January 2024 / Approved: 3 January 2024 / Online: 3 January 2024 (09:44:41 CET)
A peer-reviewed article of this Preprint also exists.
Ishihara, J. Progress in Lewis-Acid-Templated Diels–Alder Reactions. Molecules 2024, 29, 1187. Ishihara, J. Progress in Lewis-Acid-Templated Diels–Alder Reactions. Molecules 2024, 29, 1187.
Abstract
Synthesis of natural products with complicated architecture often requires segments having the functional groups that can be structurally transformed with the desired stereogenic centers. Bicyclic ?-lactones have a great potential for a suitable segment for natural product synthesis. However, the stereoselective construction of such functionalized bicyclic ?-lactones is not as straightforward as one might expect. On the other hand, the Lewis acid template-mediated Diels-Alder reaction is one of the most powerful and versatile methods for providing bicyclic ?-lactones with high regioselectivity and stereoselectivity. In this reaction, the Lewis acid template activates the dienophile as well as linking the diene and dienophile by a temporary tether. Therefore, Diels-Alder reaction smoothly proceeds in a stereocontrolled manner, allowing a simple access to bicyclic ?-lactone as a valuable building block for the synthesis of complicated natural products. In this review, some highlights of the Lewis acid-mediated Diels-Alder reaction, along with its application to the synthesis of biologically active compounds are discussed.
Keywords
Lewis acid; template; Diels-Alder reaction; natural product synthesis
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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