2007
DOI: 10.1021/ol062752p
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Synthesis of 2-Oxazolidinones from β-Lactams:  Stereospecific Total Synthesis of (−)-Cytoxazone and All of Its Stereoisomers

Abstract: The synthetic correlation between two different antibiotic frameworks, the beta-lactams and 2-oxazolidinones, is described for the first time. In this approach, 2-oxazolidinones are prepared in stereomerically pure form from 3-hydroxy beta-lactams by a ring-opening-cyclization isomerization process. Application of this methodology to the total synthesis of the cytokine modulator, (-)-cytoxazone, and its three stereoisomers is demonstrated. [reaction: see text].

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Cited by 52 publications
(33 citation statements)
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“…Some natural aminodiols exhibit marked biological activity (e.g., aristeromycin), whereas others may serve as starting materials for the synthesis of biologically active natural compounds (e.g., cytoxazone) …”
Section: Introductionmentioning
confidence: 99%
“…Some natural aminodiols exhibit marked biological activity (e.g., aristeromycin), whereas others may serve as starting materials for the synthesis of biologically active natural compounds (e.g., cytoxazone) …”
Section: Introductionmentioning
confidence: 99%
“…For example, aristeromycin, first isolated from Streptomyces citricolor , and its modified derivatives belong to an important group of carbocyclic nucleosides that exhibit a wide range of pharmacological properties such as antiviral, anticancer, and antitoxoplasma activities. Aristeromycin analogues, in particular, are widely used as antiviral agents against a range of viruses, including the human immunodeficiency, hepatitis B, herpes simplex, varicella‐zoster, influenza, and hepatitis C viruses . Other aminodiols may serve as starting materials for the synthesis of biologically active natural compounds.…”
Section: Introductionmentioning
confidence: 99%
“…Other aminodiols may serve as starting materials for the synthesis of biologically active natural compounds. For example, cytoxazone, a microbial metabolite isolated from Streptomyces species, is a selective modulator of the secretion of T H 2 cytokine …”
Section: Introductionmentioning
confidence: 99%
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“…Moreover, they are also excellent building blocks for the synthesis of various heterocyclic compounds, through participation of specific hydroxy groups in ring closure reactions with the amino group. Aminodiols have been shown to be excellent starting materials for the synthesis of both 1,3‐oxazines and spiro‐1,3‐heterocycles , , . Since the resulting heterocycles contain a free hydroxy group with coordinating ability, this may give rise to greater rigidity within a transition state, and hence to higher enantioselective induction in asymmetric transformations .…”
Section: Introductionmentioning
confidence: 99%