Total synthesis of a natural antioxidant and structure-activity relationships of related compounds.

S Jinno, N Otsuka, T Okita, K Inouye

Index: Jinno, Shuji; Otsuka, Naomi; Okita, Takaaki; Inouye, Kuniyo Chemical and Pharmaceutical Bulletin, 1999 , vol. 47, # 9 p. 1276 - 1283

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Citation Number: 7

Abstract

A total synthesis of benzodioxole derivative 1 was achieved via a palladium (0)-catalyzed cross-coupling reaction in a 68% overall yield (4 steps). A novel series of benzodioxoles bearing a variety of aromatic and heterocyclic rings was also prepared and the antioxidative activity evaluated using in vitro model systems. Structure-activity studies revealed that i) intramolecular hydrogen-bonding in the phenol moiety reduced activity, ii) introduction of ...