Synthesis of (Z, Z)-11, 13-hexadecadienal, a principal component of navel orangeworm (Pamyelois transitella) pheromone

CE Bishop, GW Morrow

Index: Bishop, Clyde E.; Morrow, Gary W. Journal of Organic Chemistry, 1983 , vol. 48, # 5 p. 657 - 660

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Citation Number: 24

Abstract

This report outlines a commercial synthetic process for (2, 2)-11, 13-hexadecadienal (navel orangeworm pheromone). The synthetic scheme which is employed introduces the stereochemically labile conjugated diene moiety at a late stage in the synthesis, thereby avoiding complications during the purification of intermediates. In addition, the aldehyde function is generated through a Grignard reaction sequence, obviating the generally ...