Synthetic studies on the validamycins. 5. Synthesis of DL-hydroxyvalidamine and DL-valienamine

Seiichiro Ogawa, Noritaka Chida, Tetsuo Suami

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A first synthesis of the peracetyl racemate (25) of hydroxyvalidamine (3), one of the degradation products of antibiotic validamycin B (1), is reported. The present result fully confirmed the proposed structure of 3. The sequence of reactions involves stereospecific peracid oxidation of the protected branched-chain unsaturated cyclitol 18 to give rise to a versatile epoxide (19) and regioselective azidolysis of 19 followed by reduction of the azido group with hydrogen sulfide. In addition, the peracetyl racemate (30) of valienamine (4) has been newly synthesized from the intermediate compound (26) of 3 by dehydration through the mesylate 27, a similar sequence of which may be generally applicable for preparation of other valienamine derivatives.

Original languageEnglish
Pages (from-to)1203-1207
Number of pages5
JournalJournal of Organic Chemistry
Volume48
Issue number8
Publication statusPublished - 1983

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Cyclitols
Hydrogen Sulfide
Mesylates
Epoxy Compounds
Dehydration
Anti-Bacterial Agents
Derivatives
Degradation
Oxidation
validamycins
valienamine
3-(5-nitrofuryl)-7-(5-nitrofurfurylidene)-3,3a,4,5,6,7-hexahydro-2H-indazole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthetic studies on the validamycins. 5. Synthesis of DL-hydroxyvalidamine and DL-valienamine. / Ogawa, Seiichiro; Chida, Noritaka; Suami, Tetsuo.

In: Journal of Organic Chemistry, Vol. 48, No. 8, 1983, p. 1203-1207.

Research output: Contribution to journalArticle

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