The synthesis of dl-prostaglandin E1 methoxime
β Scribed by Neville Finch; John J. Fitt
- Publisher
- Elsevier Science
- Year
- 1969
- Tongue
- French
- Weight
- 197 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Several groups heve recently reported on their proetaglandln eyntheels (119 (2)9
(3), ( 41, and (5). we would now like to deacrlbe e new route to thle lntereetlng femlly of compounds. Out etarting materiel 1s 2'-carboxy-5-oxo-cyclopent-1-eneheptanolc acid I, ws(CA2)e 03 s cII9W(~2)6 *.
π SIMILAR VOLUMES
Prostaglandin El has been prepared from (fi)-4-t-butyldimethylsiloxy-2-cyclopentenone by using as a key operation the tandem organocopper conjugate additionlnitroolefin Michael trapping of the resulting enolate intermediate. Regiospecific trapping with electrophiles of enolates generated from 2-cycl
An asymmetric total synthesis of Prostaglandin E 1 (5) has with the Corey CBS catalyst gave the Ο-side chain 7 with ΟΎ96% ee. Conjugate addition using the reaction with been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from dilithiocyanocuprat
Methyl ll-tert-butyldimethylsilyloxyeicosa-8~Z),l2~E),l4(E)trienoate was stereoselectively cyclized by treatment with Hg(OCOCF3j2 to give a properly functionalized PG skeleton, which was converted to PGEl in good over all yield.