Concepedia

Efficient Total Synthesis of the Pharmacophore of the Anticancer Antibiotic CC‐1065 by Zirconocene‐ and Palladium‐Initiated Cyclizations

Lutz F. Tietze, Wilm Buhr

Angewandte Chemie International Edition in English · 1995 · 54 citations · 19 references

DOI

Concepts

Abstract

Three steps suffice for constructing the pyrroloindolino framework of the pharmacophoric moiety 2 of the highly potent anticancer agent CC-1065. The easily accessible bis(allylamino)bromobenzene 1 was transformed by successive cyclizations mediated by [Cp2Zr(Me)Cl] and by a Pd° complex.

References

19

Palladium-catalysed vinylation of organic halides under solid–liquid phase transfer conditions

Tuyêt Jeffery · Journal of the Chemical Society Chemical Communications · 1984 · 464 citations

, , +11

CC-1065 (NSC-298223), a new antitumor antibiotic. Production, in vitro biological activity, microbiological assays and taxonomy of the producing microorganism.

L. J. Haňka, A Dietz, S. A. Gerpheide et al. · The Journal of Antibiotics · 1978 · 271 citations · Full text

Reaction of the antitumor antibiotic CC-1065 with DNA. Location of the site of thermally induced strand breakage and analysis of DNA sequence specificity

Vincent L. Reynolds, Ian J. Molineux, David Kaplan et al. · Biochemistry · 1985 · 202 citations

Preliminary toxicity studies with the DNA-binding antibiotic, CC-1065.

J. Patrick McGovren, George L. Clarke, Evelyn A. Pratt et al. · The Journal of Antibiotics · 1984 · 144 citations · Full text

Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI, (.+-.)-CC-1065, (+)-CC-1065, ent-(-)-CC-1065, and the precise, functional agents (.+-.)-CPI-CDPI2, (+)-CPI-CDPI2, and (-)-CPI-CDPI2 [(.+-.)-(3bR*,4aS*)-, (+)-(3bR,4aS)-, and (-)-(3bS,4aR)-deoxy-CC-1065]

Dale L. Boger, Robert S. Coleman · Journal of the American Chemical Society · 1988 · 119 citations

, , +10