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Method for the synthesis of ceralure B1

Author:
Khrimian, A.
Source:
United States Department of Agriculture patents 2004 no.US 6,777,573 B1
Subject:
insect attractants, synthesis, cyclohexenes, cyclohexanecarboxylic acids, lactones, diastereomers, esterification, chemical structure, Ceratitis capitata, fruit flies, patents, USDA, United States
Abstract:
A method has been developed for the preparation of ceralure B1, a potent attractant for the Mediterranean fruit fly. The method utilizes trans-siglure acid as starting material to produce iodolactone which is subsequently reduced to lactone. The lactone is converted to a mixture of epimers ceralure A acid and ceralure B1 acid. The ceralure A acid is recyclized to lactone, leaving epimer ceralure B1 acid intact. Following separation from lactone, the ceralure B1 acid is esterified to produce ceralure B1 of about 92-94% purity. The overall yield is about 58-65%, a significant improvement over currently known methods which result in yields of about 30-33%.
Agid:
6552
Handle:
10113/6552