Toward the total synthesis of 1,4-bis-(3-methoxy-4-hydroxyphenyl) butane

ORGN 416

Steve Marek, R. Elizabeth Brewster, and Suzanne B. Shuker. Department of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400
Until recently, it was widely believed that herbivory on freshwater macrophytes was low. Freshwater plants were thought to be low in nutritive value and to have a tough, unpalatable texture. Due to this misconception, these aquatic plants were not believed to display chemical defenses against herbivores. Recent studies, though, have shown that many freshwater plants, including the angiosperm Saururus cernuus, display these types of chemical defenses and therefore must contain toxic or unpalatable secondary metabolites. Saururus cernuus has long been used as a folk remedy for inflammation, as a sedative, and as a poultice for tumors. Additionally, Saururus cernuus has been found to deter feeding by crayfish. The lignoid metabolite (-)-dihydroguaiaretic acid, which was isolated from Saururus cernuus, was also shown to deter crayfish feeding. Currently, an analog of (-)-dihydroguaiaretic acid, 1,4-bis-(3-methoxy-4-hydroxyphenyl) butane, is being synthesized and will be screened for its ecological importance and its biological activity.
 

Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004