Helvetica Chimica Acta p. 1154 - 1167 (1984)
Update date:2022-07-31
Topics:
Oppolzer, Wolfgang
Godel, Thierry
Starting from 2-cyclopentenoyl chloride ((RS)- or (S)-8), the racemic as well as the enantiomerically pure (+)-sesquiterpenes longifolene ((+/-)- and (+)-1, resp.) and sativene ((+/-)- and (+)-2, resp.) were synthesized efficiently by a sequence of nine and ten steps, respectively.The key sequence 10 -> 16 -> 3 is the first strategic application of an intramolecular photoaddition/retro-aldolization sequence (intramolecular de Mayo reaction) in organic synthesis.
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