Enantiospecific approach toward pentalenolactone.
[reaction: see text] The enantiospecific assembly of the pentalenolactones' carbon skeleton was achieved in 17 steps and 16% overall yield from methyl alpha-D-glucopyranoside. The synthetic strategy relies on two highly efficient key steps: an exo-diastereoselective Diels-Alder reaction and a nonsymmetric ozonolysis.
Testero
Sebastian A
SA
Instituto de Química Organica de Síntesis, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
Spanevello
Rolando A
RA
D005960:Glucosides / Q000737:chemistry*; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D005960:Glucosides; D012717:Sesquiterpenes; C017996:arenaemycin E; D010126:Ozone