A group of natural products, named neolignans, has been found in Rodgersia podophylla, which has been used in Chinese medicine for thousands of years to treat intestinal and liver diseases. The common structure of these neolignans is the 1,4-benzodioxane moiety, and our goal is to develop a synthetic method towards those compounds.Our current method involves a hetero-Diels-Alder reaction starting with o-quinones, and a mixture of two regioisomers is produced. Both experimental and computational results in approaching the regioselectivity of the method will be presented.

Computational and experimental study on the synthesis of 1,4-benzodioxane via a hetero-Diels-Alder reaction

243rd National Meeting (2012)

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