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Publication 124  

  1. Synthesis of (±)-6-protoilludene and (±)-3-EPI-6-protoilludene by intramolecular magnesium-ene- and ketene/alkene addition reactions
    Oppolzer, W.; Nakao, A.
    Tetrahedron Lett. 1986, 27, 5471-5474

The sesquiterpene (±)-6-protoilludene (1) and its C(3)-epimer 11 were synthesized from aldehyde 5. The key steps are a regio- and stereo-selective type-I-magnesium-ene reaction 4→3 and an intramolecular vinylketene/alkene addition 2→9a + 9b.

DOI : 10.1016/S0040-4039(00)85240-5