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Volumn 3, Issue 19, 2001, Pages 3029-3032

Synthetic study of macquarimicins: Highly stereoselective construction of the AB-ring system

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ENZYME INHIBITOR; MACQUARIMICIN A; MACQUARIMICIN B; MACQUARIMICIN C; MACROLIDE; SPHINGOMYELIN PHOSPHODIESTERASE;

EID: 0035922346     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016449u     Document Type: Article
Times cited : (34)

References (50)
  • 13
    • 0002251962 scopus 로고
    • Curran, D. P., Ed.; JAI Press: Greenwich, CT
    • For some recent reviews on the IMDA reactions, see: (a) Roush, W. R. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 91-146.
    • (1990) Advances in Cycloaddition , vol.2 , pp. 91-146
    • Roush, W.R.1
  • 15
    • 0000048482 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford
    • (c) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 513-550.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 513-550
    • Roush, W.R.1
  • 18
    • 33947486579 scopus 로고
    • For some IMDA reactions using (E,Z,E)-trienes, see: (a) House, H. O.; Cronin, T. H. J. Org. Chem. 1965, 30, 1061-1970.
    • (1965) J. Org. Chem. , vol.30 , pp. 1061-1970
    • House, H.O.1    Cronin, T.H.2
  • 27
    • 0035932601 scopus 로고    scopus 로고
    • Very recently, effective utilization of Lewis acid catalysts in the IMDA reactions of (Z)-substituted diene has been reported, see: Yakelis, N. A.; Roush, W. R. Org. Lett. 2001, 3, 957-960.
    • (2001) Org. Lett. , vol.3 , pp. 957-960
    • Yakelis, N.A.1    Roush, W.R.2
  • 28
    • 0041771577 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR, and HRMS. Yields refer to isolated, chromatographically purified products.
  • 30
    • 0042773469 scopus 로고    scopus 로고
    • note
    • A diastereomeric mixture (1:1) of the secondary alcohols was also isolated (10%).
  • 32
    • 0041771576 scopus 로고    scopus 로고
    • note
    • Hydrolytic removal of the isopropylidene group in the TBDPS ether derived from 13 provided the corresponding diol in an unacceptable low yield.
  • 35
    • 0043274761 scopus 로고    scopus 로고
    • note
    • In our hands, the yield of 20 increased when the reaction was conducted on a larger scale. Consequently, we were able to prepare 20 on a 15 g scale with complete diastereoselectivity.
  • 39
    • 0042773468 scopus 로고    scopus 로고
    • note
    • The reductive opening of the TBDPS-protected acetal, prepared from 24 [(1) MPM acetal formation, (2) silyl ether (OTBDPS) formation], with DIBALH was accompanied by cleavage of the silyl ether.
  • 43
    • 0041771575 scopus 로고    scopus 로고
    • note
    • The overall yield of 6 from 8 was 23% and that from 19 was 16%. We prefer the second route because the isolation of 9 from other diastereomers by Chromatographic separation on silica gel was problematic in our case on a large-scale experiment.
  • 48
    • 0041771574 scopus 로고    scopus 로고
    • note
    • During a large-scale preparation of 29E, we encountered a tedious Chromatographic separation of 28E and 28Z.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.