72535-10-5Relevant academic research and scientific papers
Total Synthesis of (+/-)-Isocomene and Related Studies
Pirrung, Michael C.
, p. 82 - 87 (2007/10/02)
The total synthesis of the tricyclic sesquiterpene isocomene is described.The key bond forming reaction involves an intramolecular photocyloaddition to give tricyclo1,6>undecanone 6.Two routes are described from 6 to isocomene.The first involves acid-catalyzed rearrangement to tricyclo1,5>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.
