A total practical synthesis of (+,-)-Strigol and analogues
Abstract
An efficient synthesis of ($\pm$)-Strigol and ($\pm$)-epistrigol has been developed. Strigol is a potent seed germination stimulant for witchweed; an angiospermous root parasite of graminaceous crops. The difficulty of isolating Strigol from natural sources, has motivated efforts to develop total synthetic schemes. Three total and several partial syntheses have been reported. Our synthesis of Strigol, using commercially available alpha-ionone as the starting material, requires 10 steps and gives an overall yield of 4.4%. The synthetic scheme is applicable on a multigram scale, requires a minimum of purification steps, and allows efficient access to a number of analogues for evaluation of structure-activity-relationships. A number of analogues have been prepared from synthetic strigol intermediates, to mimic the A-A, A-B, A-D, C-D, A-B-D, A-C-D and A-B-C-D-ring partial structures of strigol. These compounds are currently in the process of evaluation as witchweed seed germination stimulants.
Degree
Ph.D.
Advisors
Brooks, Purdue University.
Subject Area
Organic chemistry
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