Synthetic studies on (+)-naphthyridinomycin: Stereoselective synthesis of the tetracyclic core framework

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3095-3097

  Mori, Kazuki ^a   Rikimaru, Kentaro ^a   Kan, Toshiyuki ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; NAPHTHYRIDINOMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; HYDROBORATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

CATALYSIS; CYCLIZATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NAPHTHYRIDINES; STEREOISOMERISM;

EID: 4544334894     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048857e     Document Type: Article

References (27)

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27. Presumably, the borane reagent attacked from the less hindered exoface of the bicyclo[3.3.1] skeleton to afford the desired stereochemistry at the C-4 position. The selective-production of both stereochemistries at C-4 would be significant, since both stereochemistries were observed in this family of natural products. The endo-oriented compounds belong to the naphthyridinomycin family (naphthyridinomycin and dnacins), while the corresponding exo-oriented compounds belong to the quinocarcin family (quinocarcin, tetrazomine, and lemonomycin). See ref 2.