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The insect pheromone (R)-sulcatol, 2-hydroxy-6-methylhept-5-ene, is synthesized via a stereoselective conjugate addition of (R)-lithium N,α-dimethylbenzylamide to tert-butyl (E,E)-hexa-2,4-dienoate, Grignard addition, and stereospecific Meisenheimer rearrangement. Hydrogenation of the olefin, dehydration of the tertiary alcohol and N-O bond cleavage complete the synthesis.

Original publication

DOI

10.1016/0957-4166(96)00103-6

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

01/01/1996

Volume

7

Pages

1005 - 1006