Decalin is one of the most predominant structural unit found in a wide variety of natural products such as polyterpenoid and steroids. Diastereo- and enantioselective synthesis of densely functionalized decalin framework has been a challenging task in synthetic chemistry. In this presentation diastereo- and enantioselective synthesis of polyfunctionalized decalins having five to six stereocenters will be discussed.<br/>Organocatalytic formal [4+2] cycloaddition reactions of dihydropyrans 1 and 1,3-diketones 2 were developed to provide densely functionalized trans-decalins 3 with high diastereo- and enantioselectivities under mild reaction conditions. Double desymmetrization of dihydropyrans 1 and 1,3-diketones led to the exclusive formation of single diastereomer of trans-decalin. Various decalin derivatives bearing up to six stereogenic centers, including two tetrasubstituted chiral carbons centers, were concisely synthesized.

Organocatalytic enantioselective synthesis of functionalized decalins <i>via</i> desymmetrization of substituted dihydropyrans and 1,3-diketones

2019 Spring National Meeting

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Organocatalytic enantioselective synthesis of functionalized decalins via desymmetrization of substituted dihydropyrans and 1,3-diketones