Syntheses of 4(R)-silyloxy-6(S)-iodomethyl-tetrahydropyran-2-one and its enantiomer, building blocks for HMG-COA reductase inhibitors
1988; Elsevier BV; Volume: 29; Issue: 21 Linguagem: Inglês
10.1016/s0040-4039(00)86112-2
ISSN1873-3581
AutoresE. Baader, Wilhelm Bartmann, G. Beck, Andreas Bergmann, H.‐W. Fehlhaber, Heiner Jendralla, Kurt Keßeler, R. SARIC, Helga Schüssler, V. Teetz, M. WEBER, Günther Wess,
Tópico(s)Plant biochemistry and biosynthesis
ResumoAbstract Optically pure 4(R), 6(S)-iodolactone 1 was obtained from α-D-(+)-glucose in 17 steps with 17% overall yield. Its enantiomer 4(S), 6(R)-iodolactone 1′ was obtained from acetonedicarboxylic acid in 9 steps in 37% overall yield and with 70% ee. Key steps in the synthesis of 1′ are enzyme (PLE)-catalyzed saponification of prochiral di-n-propyl-3-hydroxyglutarate 7 and iodolactonization of 11 .
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