✦ LIBER ✦
Syntheses of 4(R)-silyloxy-6(S)-iodomethyl-tetrahydropyran-2-one and its enantiomer, building blocks for HMG-COA reductase inhibitors
✍ Scribed by E Baader; W Bartmann; G Beck; A Bergmann; H.-W Fehlhaber; H Jendralla; K Kesseler; R Saric; H Schüssler; V Teetz; M Weber; G Wess
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 176 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Optically pure 4(R),6(S)-iodolactone 1 was obtained from a-D-(+)-glucose in 17 steps with 17% overall yield. Its enantiomere4(S),6(R)-iodolactone 1' was obtained from acetonedicarboxylic acid in 9 steps in 37% overall yield and witTi_70% ee. Key steps in the synthesis of 1' are enzyme (PLE)-catalyzed saponification of prochiral di-n-propyl-3-hydroxyglutarze 2 and iodolactonization of 11 -* R= (tert.-Bu)SiPh2
The enantiomeric iodolactones 1 and