Journal of the American Chemical Society p. 82 - 87 (1981)
Update date:2022-08-03
Topics:
Pirrung, Michael C.
The total synthesis of the tricyclic sesquiterpene isocomene is described.The key bond forming reaction involves an intramolecular <2+2> photocyloaddition to give tricyclo<6.3.0.01,6>undecanone 6.Two routes are described from 6 to isocomene.The first involves acid-catalyzed rearrangement to tricyclo<5.3.1.01,5>undecanone 7, addition of MeLi, and solvolysis, while the second uses a Wittig reaction followed by acid-catalyzed rearrangement.The question of maximum continuous orbital overlap in cyclobutyl carbinyl cation rearrangements is discussed, and certain stereochemical effects are found.
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Doi:10.1055/s-1980-29192
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