Synthetic studies on (-)-lemonomycin: Stereocontrolled construction of the 3,8-diazabicyclo[3.2.1] skeleton

Chemical Communications

Volumn , Issue 3, 2005, Pages 394-396

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLSILANE; BICYCLO COMPOUND; CYANIDE; ISOCYANIDE; LEMONOMYCIN; SILANE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; TRABECTEDIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HOSOMI SAKURAI REACTION; STEREOCHEMISTRY;

EID: 13244289856     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415030a     Document Type: Article

References (22)

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11. The selective production of both stereochemistries would be significant, since both stereochemistries were observed in this family of natural products. While the exo-oriented compounds belong to the quinocarcin family (lemonomycin, quinocarcin and tetrazomine), the corresponding endo-oriented compounds belong to the naphthyridinomycin family (naphthyridinomycin and dnacins). See ref. 2.
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20. A similar cross-metathesis with the allyl derivative of 13 (without the terminal methyl group) resulted in a low yield due to decomposition.
21. The stereochemistry was confirmed by a strong NOE between H-4 and H-15 in the Boc derivative of 19.
22. R. W. Murray and M. Singh, Org. Synth., 1998, Coll. Vol. IX, 288.