Roseophilin
Encyclopedia
Roseophilin is an antibiotic
Antibiotic
An antibacterial is a compound or substance that kills or slows down the growth of bacteria.The term is often used synonymously with the term antibiotic; today, however, with increased knowledge of the causative agents of various infectious diseases, antibiotic has come to denote a broader range of...

 isolated from Streptomyces
Streptomyces
Streptomyces is the largest genus of Actinobacteria and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described. As with the other Actinobacteria, streptomycetes are gram-positive, and have genomes with high guanine and cytosine content...

 griscovirides
shown to have antitumor activity. The chemical structure can be considered in terms of two components, a macrotricyclic segment and a heterocyclic side-chain. Several laboratory syntheses of roseophilin (e.g., those of Trost
Barry Trost
Barry M. Trost is an American chemist, Tamaki Professor of Humanities and Sciences at Stanford University....

, Furstner, Salamone) are based upon the Paal-Knorr synthesis
Paal-Knorr synthesis
The Paal–Knorr Synthesis in organic chemistry is a reaction that generates either furans, pyrroles, or thiophenes from 1,4-diketones. It is a synthetically valuable method for obtaining substituted furans and pyrroles, common structural components of many natural products...

, and two others are based on the Nazarov cyclization reaction
Nazarov cyclization reaction
The Nazarov cyclization reaction is a chemical reaction used in organic chemistry for the synthesis of cyclopentenones. The reaction is typically divided into classical and modern variants, depending on the reagents and substrates employed...

(those of Tius, Frontier).
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