Tetrahedron Letters p. 4835 - 4838 (1991)
Update date:2022-08-28
Topics:
Myles, David C.
Andrulis, Peter J.
Whitesides, George M.
The naturally occuring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps.The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of β-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5.A short sequence converted ketose 5 to protected aldose 8.Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.
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