RSS-Feed abonnieren
DOI: 10.1055/s-1999-2699
The Bis(enol triflate) Route to Dienediyne Models of the Biradical Forming and DNA-Cleaving Natural Product Neocarzinostatin Chromophore
Publikationsverlauf
Publikationsdatum:
31. Dezember 1999 (online)
![](https://www.thieme-connect.de/media/synlett/199906/lookinside/thumbnails/10.1055-s-1999-2699-1.jpg)
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