A Flexible Stereocontrolled Synthesis of β-Hydroxy-α-methyl Esters: Application to the Synthesis of Stegobiol and Serricorole

Pilar Gil; Jesús Razkin; Alberto González

doi:10.1055/s-1998-2052

Synthesis 1998; 1998(4): 386-392
DOI: 10.1055/s-1998-2052

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A Flexible Stereocontrolled Synthesis of β-Hydroxy-α-methyl Esters: Application to the Synthesis of Stegobiol and Serricorole

Pilar Gil^* , Jesús Razkin, Alberto González

^*Departamento de Química Aplicada, Universidad Pública de Navarra, Campus Arrosadía, E-31006 Pamplona, Spain; Fax + 34(48)16 95 65; E-mail: pgr@upna.es

Abstract

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β-Hydroxy-α-methyl esters have been obtained in a stereocontrolled manner and high enantiomeric and diastereomeric purity from commercially available methyl 3-oxopentanoate and methyl 3-oxobutanoate. The key step is the catalytic hydrogenation of the carbonyl group using (R)- or (S)-BINAP-Ru as chiral catalyst followed by asymmetric alkylation. Stegobiol and serricorole, components of the sex pheromone of the drugstore beetle, Stegobium paniceum (L.) and cigarette beetle, Lasioderma serricorne (F.), have been prepared from these chiral building blocks without the need for stoichiometric amounts of chiral auxiliaries.

catalytic chiral hydrogenation - (R)- and (S)-BINAP-Ru - asymmetric alkylation - stegobiol - serricorole

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