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Volumn 45, Issue 35, 2006, Pages 5837-5842

Total synthesis of iejimalide B

Author keywords

Anticancer agents; Cross coupling; Macrolides; Metathesis; Natural products

Indexed keywords

CHEMICAL BONDS; CROSSLINKING; ONCOLOGY; REACTION KINETICS; TUMORS;

EID: 33748521295     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601860     Document Type: Article
Times cited : (62)

References (71)
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    • b) the cytotoxicity data are available from the NCI homepage (http://www.dtp.nci.nih.gov/docs/dtpsearch.html).
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    • For a pertinent example of an attempted RCM prohibited by intervention of a 1,3-diene unit see: a) A. K. Ghosh, G. Gong, J. Org. Chem. 2006, 71, 1085-1093.
    • (2006) J. Org. Chem. , vol.71 , pp. 1085-1093
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    • b) a discussion and a comprehensive literature coverage of metathetic diene-ene cyclizations is found in: F. Lacombe, K. Radkowski, G. Seidel, A. Fürstner, Tetrahedron 2004, 60, 7315-7324.
    • (2004) Tetrahedron , vol.60 , pp. 7315-7324
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    • note
    • Small amounts (10-15%) of the regioisomeric alkenylstannane could be separated by flash chromatography. The corresponding pinacolborane was also prepared but failed to undergo productive cross-coupling with iodide 30.
  • 52
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    • note
    • This route to 27 was chosen for two reasons: first, problems with partial racemization were encountered when the aldehyde derived from 23 was treated with Wittig reagents in an attempt to form 28 directly; secondly, it is known that iejimalide B bearing a methyl group at C2 is more active than iejimalide A which features a proton at this position, see Ref. [2]; the chosen route via triflate 27 allows for systematic variations at this position.
  • 55
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    • c) review: A. Fürstner, Chem. Rev. 1999, 99, 991-1045.
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    • note
    • Worried that reversible double-bond isomerizations at the aldehyde stage or an equilibrium between 30 and 31 would racemize the chiral center at C4, the ee value of compound 30 was carefully checked and found to be ≥ 90%.
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    • note
    • Uncontrolled isomerizations were observed even at 35°C.
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    • Significant amounts of the symmetrical anhydride derived from acid 33 could even be isolated from the mixture; for precedents and a mechanistic discussion see: I. Dhimitruka, J. SantaLucia, Jr., Org. Lett. 2006, 8, 47-50.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.