𝔖 Bobbio Scriptorium
✦   LIBER   ✦

ChemInform Abstract: Synthesis of the Pseudoguaianolide and Guaianolide Skeleton by Cleavage of the Ether Bridge of 8-Oxabicyclo[3.2.1]octan-3-one Derivatives.

✍ Scribed by Mayura M. M. Rubinger; John Mann

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
30
Category
Article
ISSN
0931-7597

No coin nor oath required. For personal study only.

✦ Synopsis

Synthesis of the Pseudoguaianolide and Guaianolide Skeleton by

Cleavage of the Ether Bridge of 8-Oxabicyclo[3.2.1]octan-3-one Derivatives.

-The ZrCl 4 -promoted cleavage of the ether bridge of title oxabicyclooctane (I) provides, depending on the reaction conditions used, various types of polysubstituted cycloheptenones. The synthetic usefulness of this approach is demonstrated in the preparation of pseudoguaianolide derivatives (IX) and (X) starting from one of these cycloheptenones (VI). -

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Enantioselective De
ChemInform Abstract: Enantioselective Deprotonation of the 8-Oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-Oxa-norcocaines and 8-Oxa-pseudonorcocaines.
✍ Daniele Simoni; Marinella Roberti; Riccardo Rondanin; Alan P. Kozikowski πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 35 KB

Enantioselective Deprotonation of the 8-Oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-Oxa-norcocaines and 8-Oxa-pseudonorcocaines. -Asymmetric deprotonation of the racemic ketone (I) using chiral lithium amides provides ready access to the non-racemic Ξ²-ketoesters (III), which can be easily transfor