Synthetic studies on the compounds related to neocarzinostatin chromophore. 1. Synthesis of the acyclic (E)-and (Z)-dienediyne systems

Article abstract of DOI:10.1016/S0040-4020(01)88124-2

The stereo-defined (E)- and (Z)-dienediyne systems related to neocarzinostatin chromophore (1) could be prepared by the coupling reaction of (E)- and (Z)-enol triflates with optically active acetylynes bearing the correct absolute stereochemistries as found in 1. Comparison of cytotoxic level of the (E)-and (Z)-dienediyne diols (32 and 33) revealed that the stereochemistry of exo-trisubstituted double bond might have a posibility to control the cytotoxicity of the acyclic analogues related to 1.