Total synthesis of (+)-madindoline A and (-)-madindoline B, potent, selective inhibitors of interleukin 6. Determination of the relative and absolute configurations

Journal of the American Chemical Society

Volumn 122, Issue 9, 2000, Pages 2122-2123

  Sunazuka, Toshiaki ^a   Hirose, Tomoyasu ^a   Shirahata, Tatsuya ^a   Harigaya, Yoshihiro ^a   Hayashi, Masahiko ^a   Komiyama, Kanki ^a   Omura, Satoshi ^a   Smith III, Amos B ^b  

^a KITASATO UNIVERSITY   (Japan)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; INTERLEUKIN 6; MADINDOLINE A; MADINDOLINE B; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0034620786     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9938074     Document Type: Article

References (20)

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2. Richards, C. D. In Cytokines; Mire-Sluis, A. R., Thorpe, R., Eds.; Academic: San Diego, CA, 1998; pp 87-108. Hirano, T. Int. Rev. Immunol. 1998, 16, 249-284 and references therein.
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7. Hayashi, M., unpublished results.
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19. Use of (-)-DET furnished (+)-1 and (-)-2 in 15 and 34% yield, respectively. The lower selectivity vis-à-vis the model oxidation is presumably due to increased steric hindrance and/or the presence of the additional stereogenic centers in (+)-20. Oxidation with m-CPBA furnished a 1:1 mixture of (+)-1 and (-)-2.
20. The absolute configuration therefore of natural (+)-madindoline A is 3aR,8aS,2′R and (+)-madindoline B is 3aR,8aS,2′5.