An efficient synthesis of antibiotic SF-2312 (3-dihydroxyphosphoryl-1,5- dihydroxy-2-pyrrolidone)

Tadashi Hanaya, Chika Itoh

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.

Original languageEnglish
Pages (from-to)1675-1683
Number of pages9
JournalHeterocycles
Volume82
Issue number2
DOIs
Publication statusPublished - Feb 28 2010

Fingerprint

Osmium Tetroxide
Hydrogenolysis
Alkenes
Anti-Bacterial Agents
trimethylsilyl bromide
2-pyrrolidone
metaperiodate
5-hydroxy-2-pyrrolidone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

An efficient synthesis of antibiotic SF-2312 (3-dihydroxyphosphoryl-1,5- dihydroxy-2-pyrrolidone). / Hanaya, Tadashi; Itoh, Chika.

In: Heterocycles, Vol. 82, No. 2, 28.02.2010, p. 1675-1683.

Research output: Contribution to journalArticle

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