Synthesis of racemic β-chamigrene, a spiro[5.5]undecane sesquiterpene [corrected]
Simen Antonsen1, Lars Skattebøl2, Yngve Stenstrøm3
1IKBM, P.O. Box 5003, NMBU, The Norwegian University of Life Sciences, N-1430 Ås, Norway.
Abstract:
The present paper describes a total synthesis of racemic β-chamigrene, a sesquiterpene with a spiro[5.5]undecane carbon framework. Compared with previously reported β-chamigrene syntheses, we were able to reduce the total number of reaction steps, which also resulted in a significant improvement of the overall yield. The commercially available ketone 6-methylhept-5-en-2-one was transformed by known simple procedures into 3,3-dimethyl-2-methylenecyclohexanone. This reacted with isoprene by a Diels-Alder reaction to give a spiro ketone. An olefination reaction on this compound gave the target molecule.
More Related Videos
Related Concept Videos
Prochirality
Racemic Mixtures and the Resolution of Enantiomers
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Regioselectivity of Electrophilic Additions-Peroxide Effect
Stereoisomerism of Cyclic Compounds
Stereochemical Effects of Enolization


