Synthesis of Bridgehead-Functionalized Bicyclo[3.2.1]octanes via intramolecular titanium- and tributylstannane-induced pinacol coupling

✍ Scribed by Anita Egger; Jürg Hunziker; Christian Leumann; Grethy Rihs

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: German
• Weight: 634 KB
• Volume: 81
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19980810323

✦ Synopsis

Abstract

The synthesis of the enantiomerically pure, bridgehead‐functionalized bicyclo[3.2.1]octanes 11 and 16, containing a conformationally fixed trihydroxypropyl (aminodihydroxypropyl) unit, as well as the X‐ray structure of 11 are described. These compounds are of interest as sugar surrogates in the preparation of DNA analogs. Compounds 11 and 16 became available in 10 and 12 steps, respectively, and in an overall yield of 11 and 4% from D‐arabinose via a highly stereoselective pinacol coupling as the key step.