Synthesis of griseolic acid B by pi-face-dependent radical cyclization.
[reaction: see text]. Radical cyclization of 6 affords the bicyclic vinyl ether 9 with the appropriate stereochemistry for elaboration (seven steps) to griseolic acid B (1).
Knapp
S
S
Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey, Piscataway, New Jersey 08854-8087, USA. knapp@rutchem.rutgers.edu
Madduru
M R
MR
Lu
Z
Z
Morriello
G J
GJ
Emge
T J
TJ
Doss
G A
GA
D015105:3',5'-Cyclic-AMP Phosphodiesterases / Q000037:antagonists & inhibitors; D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010726:Phosphodiesterase Inhibitors / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D007202:Indicators and Reagents; D010726:Phosphodiesterase Inhibitors; C056334:griseolic acid B; D015105:3',5'-Cyclic-AMP Phosphodiesterases; D000241:Adenosine