Synthesis of (+)-nocardione A--use of formal radical cyclization onto a benzene ring.
Juglone (7) was converted into enone 13; this underwent radical cyclization to afford 15, which was aromatized to 16 and elaborated into (+)-nocardione A (1), the enantiomer of the naturally-occurring tyrosine phosphatase inhibitor (-)-nocardione A (2).
Clive
Derrick L J
DL
Chemistry Department, University of Alberta, Edmonton, Alberta, Canada T6G 2G2. derrick.clive@ualberta.ca
Fletcher
Stephen P
SP
D001554:Benzene / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology
D005663:Furans; D009285:Naphthoquinones; C410782:nocardione A; D001554:Benzene