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Synlett 1999; 1999(6): 657-679
DOI: 10.1055/s-1999-2699
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The Bis(enol triflate) Route to Dienediyne Models of the Biradical Forming and DNA-Cleaving Natural Product Neocarzinostatin Chromophore

Reinhard Brückner* , Jean Suffert
  • *Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Albertstraße 21, D-79104 Freiburg, Germany; Fax +49-7 61-2 03 61 00; E-mail: reinhard.brueckner@organik.chemie.uni-freiburg.de
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Publication Date:
31 December 1999 (online)

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The exceedingly cyctotoxic compound neocarzinostatin chromophore continues to fascinate chemists and biologists. Several groups have set out to synthesize this molecule and/or simplified functional analogues thereof. Pertinent work of our groups is compiled in the following. As an entry to the Z-dienediyne systems we employed Cacchi couplings between the bis(enol triflates) Z-34 or Z-35 and terminal alkynes. From there, we synthesized type-21 and type-22 dienediynes. They engaged in neocarzinostatin-type cycloaromatizations 23 → 25 and 24 → 26, respectively. In addition, we prepared dienediynes of general structures 27 or 28. They were carried on to Saito-Myers cyclizations 29 → 31 and 30 → 32, respectively.

C,C coupling - dienediynes - enediyne antibiotics - enol triflate - neocarzinostatin