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ChemInform Abstract: Application of the Stereoselective Diels-Alder Reaction of Enantiopure 2-Sulfinyl Dienes: Synthesis of (-)-(1S,5R)-Karahana Ether.

✍ Scribed by P. GOSSELIN; E. BONFAND; C. MAIGNAN

Publisher: John Wiley and Sons
Year: 2010
Weight: 31 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199735230

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✦ Synopsis

Application of the Stereoselective Diels-Alder Reaction of Enantiopure 2-Sulfinyl Dienes: Synthesis of (-)-(1S,5R)-Karahana Ether.

-The natural karahana ether (VII) is synthesized for the first time by application of sulfinyl derivative (I) as chiral auxiliary in asymmetric Diels-Alder reaction and of sulfoxide activating influence in intramolecular heteroatom addition, leading to bicycle (VI). The sulfoxide group is cleanly removed with Raney-

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