A stereoconvergent intramolecular Diels-Alder cycloaddition related to the construction of the decalin core of neo-clerodane diterpenoids.

Sean C Butler, Craig J Forsyth

Department of Chemistry, The University of Texas at Tyler, Tyler, Texas 75799, USA. sbutler@uttyler.edu

The Journal of organic chemistry 2013 Apr 19

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Several examples of a highly specific, stereoconvergent intramolecular Diels-Alder cycloaddition that led to the trans-decalin core of neo-clerodane diterpenoids are described. The relative configuration adjacent to the dienophile, which led to C4 of the decalin system, as well as the electron-withdrawing effects of various substituents and conformational rigidity of the Diels-Alder precursors were explored.

Citation

Sean C Butler, Craig J Forsyth. A stereoconvergent intramolecular Diels-Alder cycloaddition related to the construction of the decalin core of neo-clerodane diterpenoids. The Journal of organic chemistry. 2013 Apr 19;78(8):3895-907