A simple stereoselective synthesis of the cholesterol absorption inhibitor (-)-SCH 48461
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.
Stereoselective synthesis of 2-azetidinones as cholesterol-absorption inhibitors
The synthesis of two 2-azetidinones possessing powerful cholesterol- absorption inhibition properties has been accomplished by a short and highly stereoselective reaction sequence. The key step is the condensation of the titanium enolate of the easily prepared 2-pyridylthioester (R)-11 with imine 6 which affords the desired β-lactam intermediate in the correct relative and absolute configuration. Conversion to the pharmacologically active compounds is readily accomplished by simple functional group manipulation. (C) 2000 Elsevier Science Ltd.
Asymmetric Synthesis and Absolute Stereochemistry of Cholesterol Absorption Inhibitor, SCH 484661.
The first asymmetric synthesis of cholesterol absorption inhibitor, SCH 48461 is described.The compound was prepared from an asymmetric ester enolate-imine condensation using Oppolzer's chiral ester or the corresponding menthol ester as the stereocontroll
Burnett, Duane A.
p. 7339 - 7342
(2007/10/02)
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