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ChemInform Abstract: 2,3,6,7-Tetrasubstituted Perhydroanthracenes: Stereoselective Synthesis and Biconformationality Studies.

✍ Scribed by Joern Berninger; Rolf Krauss; Hans-Georg Weinig; Ulrich Koert; Burkhard Ziemer; Klaus Harms

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

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✦ Synopsis

Stereoselective

Synthesis and Biconformationality Studies.

-The title perhydroanthracene (X) with the relative conformation 2Ξ²,3Ξ±,4aΞ±,6Ξ²,7Ξ±,8aΞ²,9aΞ±,10aΞ² is stereoselectively synthesized involving three diastereoselective cycloaddition steps followed by introduction of the terminal hydroxy groups via epoxide (VIII), and Barton-McCombie deoxygenation as key steps. The biconformationality of compound (X) is studied using NMR and X-ray techniques. Simultaneous desilylation-bisacetal formation of compound (X) on reaction with tetramethoxybutane (XI) induces a hitherto not described conformational triple ring flip within the tetrasubstituted anthracene molecule. -(BERNINGER,

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Diastereoselective
ChemInform Abstract: Diastereoselective Synthesis of Tetrasubstituted-Octahydro-3,6-diazacarbazoles and Tetrasubstituted-3,6-diazacarbazoles via Double Pictetβ€”Spengler Reaction.
✍ Abdullah M. A. Shumaila; Vedavati G. Puranik; Radhika S. Kusurkar πŸ“‚ Article πŸ“… 2011 πŸ› John Wiley and Sons βš– 38 KB

## Abstract A novel synthesis of tetrasubstituted 3,6‐diazacarbazoles of type (VII) involves a diastereoselective formation of the octahydro derivatives (VI).