Enantiospecific syntheses of valienamine and 2-epi-valienamine

Tony K.M. Shing, Tin Y. Li, Stanton H.L. Kok

Research output: Contribution to journalArticlepeer-review

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

ASJC Scopus subject areas

  • Organic Chemistry

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