A new stereocontrolled synthetic route to (-)-echinosporin from D-glucose via Padwa allenylsulfone [3 + 2]-anionic cycloadditive elimination.
A new formal total synthesis of (-)-echinosporin has been developed based upon the Padwa [3 + 2]-cycloadditive elimination reaction of allenylsulfone 4 with the D-glucose-derived enone 14 which provides cycloadduct 12.
The School of Chemistry and Chemical Engineering, and the CCRCB, Queen's University Belfast, Stranmillis Road, Belfast BT9 5AG, Northern Ireland, UK.
Jakub T
JT
Flasz
Karl J
KJ
Hale
D000466:Alkadienes / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D000466:Alkadienes; D000838:Anions; D004952:Esters; D007783:Lactones; D013450:Sulfones; C025947:propadiene; C034567:echinosporin; D005947:Glucose