An Efficient Asymmetric Synthesis of Prostaglandin E1
✍ Scribed by Ana Rodríguez; Miguel Nomen; Bernd Werner Spur; Jean-Jacques Godfroid
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 364 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
An asymmetric total synthesis of Prostaglandin E 1 (5) has with the Corey CBS catalyst gave the ω-side chain 7 with Ͼ96% ee. Conjugate addition using the reaction with been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A ester 22 gave (-)-PGE 1 5 in high yield. catalytic asymmetric reduction of the γ-iodo vinyl ketone 19 [a] Department of Cell Biology, University of Medicine and Denti-Ϫ100°C (88% ee), [14] CBS at room temperature (93% stry of New Jersey, SOM ee), [15] YamamotoЈs diisobutylaluminum-2,6-di-tert-butyl-
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