A synthetic approach to the fusicoccane A-B ring fragment based on a Pauson-Khand cycloaddition/Norrish type 1 fragmentation.
A synthetic approach to the A-B ring system within the fusicoccane family of diterpenes is presented. Key steps in this approach are a diastereoselective Pauson-Khand reaction, a Norrish 1 photofragmentation, a Charette cyclopropanation, and a ring-closing metathesis process.
Dake
Gregory R
GR
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, BC, Canada, V6T 1Z1.gdake@chem.ubc.ca
Fenster
Erik E
EE
Patrick
Brian O
BO
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010777:Photochemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D004224:Diterpenes; C533054:fusicoccane A; C533055:fusicoccane B; C030797:cyclopropane