A four-step synthesis of the hydroazulene core of guanacastepene.
[reaction: see text] A concise, four-step conversion of 2-methylcyclopentenone to hydroazulene 2 is described. An alternative approach that led to an unexpected [5,5]-bicyclic carbon framework is also discussed.
Dudley
G B
GB
The Laboratory for Bioorganic Chemistry, The Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.
Danishefsky
S J
SJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D052176:Azulenes; D003508:Cycloheptanes / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*
C433947:2-methylcyclopentenone; D000900:Anti-Bacterial Agents; D052176:Azulenes; D003508:Cycloheptanes; D003517:Cyclopentanes; D004224:Diterpenes; C409194:guanacastepene; C005525:azulene