A 4 + 3 cycloaddition approach to the synthesis of spatol. A formal total synthesis of racemic spatol.
[reaction: see text] A formal total synthesis of racemic spatol is presented. The key steps involved a 4 + 3 cycloaddition of a halogenated cyclopentenyl cation to cyclopentadiene and a quasi-Favorskii rearrangement.
Harmata
M
M
Department of Chemistry, University of Missouri-Columbia, 65211, USA. harmatam@missouri.edu
Rashatasakhon
P
P
D017607:Aluminum Compounds; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D018020:Lithium Compounds; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D000459:Phaeophyceae / Q000737:chemistry*
D017607:Aluminum Compounds; D000970:Antineoplastic Agents; D004224:Diterpenes; D007202:Indicators and Reagents; D018020:Lithium Compounds; C434310:spatol; C042073:lithium aluminum hydride