Enantiospecific syntheses of valienamine and 2-epi-valienamine

Tony Kung Ming Shing, Tin Y. Li, Stanton H.L. Kok

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Cyclic sulfite 10, readily available from (-)-quinic acid (3) in 10 steps, was ring opened regio- and stereospecifically with azide anion to give (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene- 2,3,4-triol (11). Deprotection of 11 afforded, for the first time, 2- epivalienamine (2), which was isolated as penta-N,O-acetyl-2-epi-valienamine (14). The configuration of the free hydroxy group in 11 was inverted by a two-step sequence to give the blocked valienamine 19 that was deprotected to give valienamine (1), isolated as penta-N,O-acetylvalienamine (21). This approach furnished (+)-valienamine (1) in 16 steps (7% overall yield) and recorded the first synthesis of 2-epi-valienamine (2) in 13 steps (11% overall yield).

Original languageEnglish
Pages (from-to)1941-1946
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number6
DOIs
Publication statusPublished - 1999 Mar 19
Externally publishedYes

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Quinic Acid
Sulfites
Azides
Anions
valienamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantiospecific syntheses of valienamine and 2-epi-valienamine. / Shing, Tony Kung Ming; Li, Tin Y.; Kok, Stanton H.L.

In: Journal of Organic Chemistry, Vol. 64, No. 6, 19.03.1999, p. 1941-1946.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Li, Tin Y. ; Kok, Stanton H.L. / Enantiospecific syntheses of valienamine and 2-epi-valienamine. In: Journal of Organic Chemistry. 1999 ; Vol. 64, No. 6. pp. 1941-1946.
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