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Titolo:
NOVEL TRANSANNULAR REARRANGEMENTS OF AZALIDE IMINOETHERS
Autore:
WILKENING RR; RATCLIFFE RW; DOSS GA; MOSLEY RT; BALL RG;
Indirizzi:
MERCK & CO INC,MERCK SHARP & DOHME RES LABS,DEPT MED CHEM,POB 2000 RAHWAY NJ 07065 MERCK & CO INC,MERCK SHARP & DOHME RES LABS,DEPT DRUG METAB RAHWAY NJ07065 MERCK & CO INC,MERCK SHARP & DOHME RES LABS,DEPT MOL DIVERS & DESIGN RAHWAY NJ 07065
Titolo Testata:
Tetrahedron
fascicolo: 50, volume: 53, anno: 1997,
pagine: 16923 - 16944
SICI:
0040-4020(1997)53:50<16923:NTROAI>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
HOMONUCLEAR CROSS-POLARIZATION; TWO-DIMENSIONAL NMR; BECKMANN REARRANGEMENT; ERYTHROMYCIN-A; COHERENCE TRANSFER; SHIFT CORRELATION; SPECTROSCOPY; DERIVATIVES; SPECTRA; OXIME;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
44
Recensione:
Indirizzi per estratti:
Citazione:
R.R. Wilkening et al., "NOVEL TRANSANNULAR REARRANGEMENTS OF AZALIDE IMINOETHERS", Tetrahedron, 53(50), 1997, pp. 16923-16944

Abstract

The transannular reactions between the aglycone hydroxyl groups and the iminoether and lactone groups of the 9a- and 8a-azalide iminoethers4 and 5 were investigated under a variety of conditions. Translactonization by the Il-hydroxyl groups of 4 and 5 were found to give the corresponding 13-membered iminoethers 21 and 9. The thermal rearrangementof 4 produced an epimeric mixture of the 9,11-iminoethers 15 and 16. Further elaboration of isomer 16 produced 8-epi azithromycin 20. Finally, we have proposed an alternative structure, the amino gamma-lactone25, for one of the reported products (14) from the Beckmann rearrangement of erythromycin A (9E)-oxime 13. An authentic sample of 9a-aza-9a-homoerythromycin A 14 was prepared in three steps from iminoether 4. (C) 1997 Elsevier Science Ltd.

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Documento generato il 18/11/17 alle ore 05:51:43