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Synlett 1994; 1994(1): 51-53
DOI: 10.1055/s-1994-22735
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The Synthesis and Acid Induced Cycloaromatization of a Dienediyne Analog of Neocarzinostatine Chromophore

J. Suffert* , R. Brückner
  • *Laboratoire de Phannacochimie Moléculaire, Centre de Neurochimie du CNRS, 5 rue Blaise Pascal, F-67084 Strasbourg cedex, France.
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22. März 2002 (online)

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Dienediyne 17 was synthesized from the monoprotected diyne 12 and the earlier described cyclopentanone-based bis(enoltriflate) 11 through Pd(0)/Cu(I) catalyzed coupling reactions (6 steps from o-bromo benzaldehyde). Treatment of 17 with camphor sulphonic acid, EtSH, and 1,4-cyclohexadiene at 37°C furnished 31 % of the cyclopenta[b]phenanthrene 18 through a cycloaromatization.