Formal synthesis of the antitumour antibiotic CC-1065
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 2491-2499
- https://doi.org/10.1039/p19880002491
Abstract
A formal total synthesis of the potent antitumour antibiotic CC-1065 (1) is described; both the cyclopropapyrroloindole (2) and the ‘dimeric’ pyrroloindole (3) are synthesized by routes involving vinyl azide chemistry. The cyclopropapyrroloindole (2) is prepared from 5-benzyloxy-2-bromoacetophenone (Schemes 3–5), the key steps being the formation of both indoles by decomposition of the azides (9) and (13). The dimer (3) is prepared by coupling the monomeric pyrroloindoles (25) and (27), followed by functional group transformations (Scheme 7).This publication has 10 references indexed in Scilit:
- Studies on the synthesis of the antitumor agent CC-1065. Synthesis of PDE I and PDE II, inhibitors of cyclic adenosine-3',5'-monophosphate phosphodiesterase using the 3,3'-bipyrrole strategyJournal of the American Chemical Society, 1987
- Studies on the total synthesis of CC-1065: preparation of a synthetic simplified 3-carbamoyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole dimer/trimer/tetramer (CDPI dimer/trimer/tetramer) and development of methodology for PDE-I dimer methyl ester formationThe Journal of Organic Chemistry, 1987
- Studies on the synthesis of the antitumor agent CC-1065. Synthesis of the unprotected cyclopropapyrroloindole A portion using the 3,3'-bipyrrole strategyJournal of the American Chemical Society, 1987
- Diels-Alder reactions of heterocyclic azadienes: total synthesis of PDE I, PDE II, and PDE I dimer methyl esterJournal of the American Chemical Society, 1987
- Photocyclization strategy for the synthesis of antitumor agent CC-1065: synthesis of dideoxy PDE-I and PDE-II. Synthesis of thiophene and furan analogs of dideoxy PDE-I and PDE-IIThe Journal of Organic Chemistry, 1987
- Vinyl azides in heterocyclic synthesis. Part 8. Synthesis of the naturally occurring phosphodiesterase inhibitors PDE-I and PDE-IIJournal of the Chemical Society, Perkin Transactions 1, 1987
- Diels-Alder reactions of heterocyclic azadienes: total synthesis of PDE-II methyl esterThe Journal of Organic Chemistry, 1986
- Intramolecular Diels-Alder reactions of 1,2-diazines: general indoline synthesis. Studies on the preparation of the central and right-hand segments of CC-1065The Journal of Organic Chemistry, 1984
- The structure of CC-1065, a potent antitumor agent and its binding to DNAJournal of the American Chemical Society, 1981
- CC-1065 (NSC-298223), a new antitumor antibiotic. Production, in vitro biological activity, microbiological assays and taxonomy of the producing microorganism.The Journal of Antibiotics, 1978