The Structure and Chemistry of Actidione, an Antibiotic from Streptomyces Griseus

Kornfeld, Edmund C.; Jones, Reuben G.; Parke, Thomas V.

doi:10.1021/ja01169a041

Cited by 84 publications

(21 citation statements)

References 3 publications

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“…Lactones of this type have been reported (12) to arise from glutarimide antibiotics under strongly acidic or basic conditions, and we encountered the same in our prior work (1). The second compound was the unsaturated ketone 5, characterized by irpeaks at 1730, 1710, 1689, and 1645 cm-', a uv maximum at 242 nm, and an nmr signal at 6 6.5 (m, 1H) for the vinylic proton.…”

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confidence: 71%

Notes on the directed aldol synthesis and reduction of some compounds related to cycloheximide

Piatak¹,

Tang²

1987

Can. J. Chem.

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DAVID M. PIATAK and PUI-FUN LOUISA TANG. Can. J. Chem. 65, 1327Chem. 65, (1987. Several N-phenylcycloheximide analogues were prepared by TiCI4-promoted aldol condensation between trimethylsilyl en01 ethers of cyclic ketones and (N-phenylg1utarirnide)-P-acetaldehyde. Favored stereoisomers were isolated in several instances and identified from nuclear magnetic resonance data. Only for the analogue from 4-tert-butylcyclohexanone was it possible to obtain both erythro and threo isomers. Catalytic reduction of the P-hydroxyketone system overPtOz gave dihydrocycloheximide analogues possessing an axial ring hydroxyl group. Reduction in glacial HOAc was noted as promoting fission of the glutarimide ring with formation of lactone amides and, in several instances, concomitant reduction of the phenyl ring to a cyclohexyl group. DAVID M. PIATAK et PUI-FUN Loursa TANG. Can. J. Chern. 65, 1327Chern. 65, (1987.On a prtpart plusieurs analogues de la N-phtnylcycloheximide en proctdant a la condensation aldolique, catalyste par le TiC14, d'tthers Cnoliques trirntthylsilyles de cttones cycliques et de (N-phtnylg1utarimide)-P-acttaldthyde. Dans plusieurs cas, on a isolt les sttrtoisombres les plus favorists et on les a caracttrists par la rtsonance magnttique nucltaire. L'analogue de la tert-butyl-4 cyclohexanone est le seul cas oh I'on a pu isoler les isomeres tant trythro que thre'o. La reduction catalytique du systkme P-hydroxycttonique, a l'aide de Pt02, conduit aux analogues dihydrocycloheximides posstdant un groupement hydroxyle axial. On a note que la reduction dans I'acide acttique glacial favorise une fission du noyau glutarimide qui conduit B la formation d'amides lactoniques et, dans plusieurs cas, a une rtduction concomitante du noyau phtnyle en groupernent cyclohexyle.[Traduit par la revue]Our prior work (1) with analogues of the antibiotic and DNA biosynthetic inhibitor cycloheximide l a indicated that these compounds held some promise as potential anticonvulsants. A general synthetic procedure leading regio-and stereospecifically to the requisite P-hydroxyketone functionality was sought, since the previous methods we used were not as simple and direct as we had hoped. We began by examining the TiC14-promoted directed aldol condensation procedure, initially described by T. Mukaiyama et al. (2), to develop an efficient strategy for the synthesis of additional analogues whereby the cyclohexane ring substituents and (or) the imide ring portion of the molecule could be varied before introducing the P-hydroxyketone system. Recently, S. Kudo et al. (3,4) used titanium and tin halide mediated methods to prepare optically active tratzs-cycloheximide isomers and chiral cis-cycloheximide isomers for antimicrobial activity studies. Thus, the method offered promise.Our initial experience with the Mukaiyama procedure using the glutarimide-P-acetaldehyde (5) was unsatisfactory as we were unable to effect adequate protection of the imide group with benzyl chloride. Direct reaction of the imidealdehyde and 6-methyl-1-trimethylsil...

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confidence: 71%

Notes on the directed aldol synthesis and reduction of some compounds related to cycloheximide

Piatak¹,

Tang²

1987

Can. J. Chem.

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“…This general scheme was followed here for 2,4,6-and 2,4,8-trimethylDBT. As an alternative, we were interested in finding out whether phosphorus pentoxide in methanesulfonic acid [8] could be usefully employed instead of PPA and therefore the other compounds were prepared using this reagent for the ring closure. In Figure 1 this procedure is illustrated for 1,4,7-trimethylDBT.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Seven Trimethyldibenzothiophenes

Andersson

Schräder

Traulsen

et al. 2001

Polycyclic Aromatic Compounds

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“…1 ,2) The antibiotics commonly contain a glutarimide ring in their structures. 13 A new antibiotic, ES,which has twonitrogen atoms in its structure, had weak antifungal and strong inhibitory activity ag~inst lymphocyte blastogenesis. ACHX showed similar biological activities as ES, i.e., weak antifungal and strong anti-blastogenesis activĩ ties.…”

Section: Discussionmentioning

confidence: 99%

Epiderstatin and Its Related Glutarimide Antibiotics Inhibit the Cell Growth Induced by Mitogen Stimulation

Sonoda¹,

Osada²,

Magae³

et al. 1990

Agricultural and Biological Chemistry

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The Structure and Chemistry of Actidione, an Antibiotic from Streptomyces Griseus

Cited by 84 publications

References 3 publications

Notes on the directed aldol synthesis and reduction of some compounds related to cycloheximide

Notes on the directed aldol synthesis and reduction of some compounds related to cycloheximide

Synthesis of Seven Trimethyldibenzothiophenes

Epiderstatin and Its Related Glutarimide Antibiotics Inhibit the Cell Growth Induced by Mitogen Stimulation

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