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Asymmetric Diels-Alder reaction is one step in the biosynthesis of the statin lovastatin. [60] The retro-Diels–Alder reaction is used in the industrial production of cyclopentadiene. Cyclopentadiene is a precursor to various norbornenes, which are common monomers. The Diels–Alder reaction is also employed in the production of vitamin B6.
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For example, an analog for the Diels-Alder reaction is the quadricyclane-DMAD reaction: In the (i+j+...) cycloaddition notation i and j refer to the number of atoms involved in the cycloaddition. In this notation, a Diels-Alder reaction is a (4+2)cycloaddition and a 1,3-dipolar addition such as the first step in ozonolysis is a (3+2)cycloaddition.
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The first reaction in the sequence is a DA INV reaction between the tetrazine and vinyl acetal, followed by a retro-Diels–Alder reaction to afford a 1,2-diazine product. After several more steps, an intramolecular DA INV reaction occurs, followed again by a retro Diels-Alder in situ, to afford an indoline product. This indoline is a converted ...