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Tandem dienone photorearrangement-cycloaddition for the rapid generation of molecular complexity.

ABSTRACT: A tandem dienone photorearrangement-cycloaddition (DPC) reaction of novel cyclohexadienone substrates tethered with various 2? and 4? reaction partners resulted in the formation of polycyclic, bridged frameworks. In particular, use of alkynyl ether-tethered substrates led to (3 + 2) cycloaddition to afford strained alkenes which could be further elaborated by intra- and intermolecular cycloaddition chemistry to produce complex, polycyclic chemotypes.

SUBMITTER: Bos PH

PROVIDER: S-EPMC3964885 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Tandem dienone photorearrangement-cycloaddition for the rapid generation of molecular complexity.

Bos Pieter H PH Antalek Mitchell T MT Porco John A JA Stephenson Corey R J CR

Journal of the American Chemical Society 20131113 47

A tandem dienone photorearrangement-cycloaddition (DPC) reaction of novel cyclohexadienone substrates tethered with various 2π and 4π reaction partners resulted in the formation of polycyclic, bridged frameworks. In particular, use of alkynyl ether-tethered substrates led to (3 + 2) cycloaddition to afford strained alkenes which could be further elaborated by intra- and intermolecular cycloaddition chemistry to produce complex, polycyclic chemotypes. ...[more]

PMID: 24161069

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