Thallium(III) in Organic Synthesis

Abstract

A review concerning the applications of thallium(III) in organic synthesis is presented. The last ten years (1989)(1990)(1991)(1992)(1993)(1994)(1995)(1996)(1997)(1998) are exhaustively reviewed showing the recent advances of the useful reactions promoted by this versatile oxidizing reagent.

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics

“…232–244 The reason behind the growing concern in this area is the abundance of this bicycle in natural products and their metabolites 245,246 and their use as precursors for the synthesis of other important bicycles. For example, thallium( iii ) nitrate-promoted oxidative rearrangements are well documented in this regard in the recent literature, 247 and its successful application in bicyclo[3.3.1]nonane chemistry was first demonstrated by Butkus and coworkers. During the beginning of this century, his team efficiently synthesized chiral tricyclo[4.3.0.0 3,8 ]nonane-4,5-dione from enantiopure bicyclo[3.3.1]nonane-2,6-dione employing this oxidation protocol.…”

A Short Route to (−)-Mintlactone by Thallium(III)-Mediated Cyclization of (−)-Isopulegol

“…In conclusion, a very short synthesis of (−)-mintlactone 1 has been achieved starting from commercially available (−)-isopulegol; this route proved superior in all aspects to the alternative procedure, recently reported by us, starting from carboxylic acids. Moreover, the approach here described is a further example of the usefulness of the thallium (III) salts in organic synthesis …”