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Volumn 4, Issue 5, 2002, Pages 783-786

Spongistatin synthetic studies. An efficient, second-generation construction of an advanced ABCD intermediate

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ETHER DERIVATIVE; LACTONE; MACROLIDE; SPONGISTATIN 1;

EID: 0037035004     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017273z     Document Type: Article
Times cited : (93)

References (50)
  • 14
    • 85034523432 scopus 로고    scopus 로고
    • See ref 8a and also ref 9 for a list to date of synthetic studies towards the spongistatins
    • See ref 8a and also ref 9 for a list to date of synthetic studies towards the spongistatins.
  • 29
    • 85034521660 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 35
    • 85034523618 scopus 로고    scopus 로고
    • Initial studies employing the tosyl hydrazone did not lead to the desired deprotonation
    • Initial studies employing the tosyl hydrazone did not lead to the desired deprotonation.
  • 36
    • 85034523944 scopus 로고    scopus 로고
    • The use of tosyl imidazole, a more commonly employed reagent for this type of transformation, led to competitive sulfonation of the secondary hydroxyl after epoxide formation, as well as recovered starting material
    • The use of tosyl imidazole, a more commonly employed reagent for this type of transformation, led to competitive sulfonation of the secondary hydroxyl after epoxide formation, as well as recovered starting material.
  • 38
    • 0000180260 scopus 로고    scopus 로고
    • Large-scale preparation of this valuable intermediate was carried out using Jacobsen's kinetic resolution methodology: see: Furrow, M. E.; Schaus. S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 68, 6776.
    • (1998) J. Org. Chem. , vol.68 , pp. 6776
    • Furrow, M.E.1    Schaus, S.E.2    Jacobsen, E.N.3
  • 41
    • 85034523416 scopus 로고    scopus 로고
    • Treatment with both chelating and nonchelating Lewis acids only afforded a 2.6-2.2:1 ratio of anti/syn diastereomers
    • Treatment with both chelating and nonchelating Lewis acids only afforded a 2.6-2.2:1 ratio of anti/syn diastereomers.
  • 46
    • 85034521883 scopus 로고    scopus 로고
    • A 20:1 mixture of diastereomers was obtained. This minor diastereomer resulted from competitive tosylation at the secondary hydroxyl followed by displacement of the tosylate
    • A 20:1 mixture of diastereomers was obtained. This minor diastereomer resulted from competitive tosylation at the secondary hydroxyl followed by displacement of the tosylate.
  • 47
    • 85034527618 scopus 로고    scopus 로고
    • The reaction proved sensitive to oxygen on small scale. Use of oxyclear argon improved the reproducibility of the reaction
    • The reaction proved sensitive to oxygen on small scale. Use of oxyclear argon improved the reproducibility of the reaction.
  • 50
    • 85034527702 scopus 로고    scopus 로고
    • We thank Professor I. Paterson for providing spectroscopic data for the correlation compound
    • We thank Professor I. Paterson for providing spectroscopic data for the correlation compound.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.