ChemInform Abstract: Synthetic Approaches to Pseudopterosin G Aglycone Dimethyl Ether.

✍ Scribed by J.-Y. LEBRAZIDEC; P. J. KOCIENSKI; J. D. CONNOLLY; K. W. MUIR

• Book ID: 101877543
• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 45 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199850120

✦ Synopsis

Synthetic Approaches to Pseudopterosin G Aglycone Dimethyl

Ether.

-The enantiomeric aglycone dimethyl ether (XII) of the potent marine antiinflammatory pseudopterosin G is prepared using successive reactions of a dimethoxy arene with allylic cation equivalents for the construction of the hexahydro-1H-phenalene system. Noteworthy features of this approach are the creation of the (6S) stereochemistry by regio-and enantiofacially-selective nucleophilic addition of an arylmetal to the homochiral η 3 -allyl cationic complex (II) and the control of the three subsequent stereogenic centers by stereorelay.