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Publication 70  

  1. A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)-modhephene. Preliminary communication
    Oppolzer, W.; Marazza, F.
    Helv. Chim. Acta 1981, 64, 1575-1578

The unusual propellane skeleton of the sesquiterpene modhephene (1) has been synthesized starting from cyclopentenone (2). The key step 6 → 7 is an efficient and highly stereoselective intramolecular thermal ene-reaction. Further elaboration of the propellane 7 gave the enone 10 which had been previously converted to (±)-modhephene (1) in three steps.

DOI : 10.1002/hlca.19810640537