Total synthesis of (+/-)-13-methoxy-15-oxozoapatlin, a rearranged kaurane diterpenoid.
A 21-step linear synthesis of the structurally novel and biologically intriguing diterpenoid (+/-)-13-methoxy-15-oxozoapatlin (6) is described. Of particular note in this work is the development of a new method for the construction of the functionalized bicyclo[3.2.1]octane unit present in the target substance.
Britton
Robert A
RA
Department of Chemistry, University of British Columbia, Vancouver, British Columbia, Canada V6T 1Z1.
Piers
Edward
E
Patrick
Brian O
BO
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D045786:Diterpenes, Kaurane / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009795:Octanes / Q000737:chemistry; D013237:Stereoisomerism
C099330:13-methoxy-15-oxozoapatlin; D001643:Bridged Bicyclo Compounds; D004224:Diterpenes; D045786:Diterpenes, Kaurane; D009795:Octanes