Transformation of D-(-)-ribose into a natural product-like scaffold via a Lewis acid catalyzed intramolecular hetero-Diels-Alder reaction.
Starting from D-(-)-ribose, a tricyclic natural product-like scaffold suitable for combinatorial derivatization was synthesized via an intramolecular hetero-Diels-Alder reaction. Lithium perchlorate was found to enhance the reaction rate and, at the same time, had a pronounced influence on the chemoselectivity of the reaction. The stereochemical course of the reaction, however, was not influenced by the Lewis acid.
Messer
Roland
R
Department of Chemistry and Biochemistry, University of Bern, Bern, Switzerland.
Fuhrer
Cyril A
CA
Häner
Robert
R
D000143:Acids / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007536:Isomerism; D007700:Kinetics; D018020:Lithium Compounds / Q000737:chemistry; D017616:Magnesium Compounds / Q000737:chemistry; D008956:Models, Chemical; D009942:Organometallic Compounds; D010472:Perchlorates / Q000737:chemistry; D012266:Ribose / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry
D000143:Acids; D001688:Biological Products; D018020:Lithium Compounds; D017616:Magnesium Compounds; D009942:Organometallic Compounds; D010472:Perchlorates; D012266:Ribose; C102815:titanium isopropoxide; C016547:magnesium perchlorate; C025096:titanium tetrachloride; D014025:Titanium; C054684:lithium perchlorate