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Synthesis 1996; 1996(7): 819-820
DOI: 10.1055/s-1996-4302
short paper
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A Simple Stereoselective Synthesis of the Cholesterol Absorption Inhibitor (-)-SCH 48461

Manfred Braun* , Dietmar Galle
  • *Institut für Organische Chemie und Makromolekulare Chemie der Universität Düsseldorf, D-40225 Düsseldorf, Germany, Fax +49(211)8113085; E-mail: braunm@clio.rz.uni-duesseldorf.de
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Publication Date:
31 December 2000 (online)

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The cholesterol absorption inhibitor (3R,4S)-1 is synthesized in 91% ee by a stereoselective condensation of doubly deprotonated ester 2 and imine 3. The optical purity of the trans-diastereomer 1 obtained as the major isomer (trans/cis, 94:6) is enhanced to > 98% ee by a single recrystallization.

esterenolate-imine condensation - 1,1,2-triphenylethane-1,2-diol - β-lactam - circular dichroism

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