메뉴 건너뛰기




Volumn 1, Issue 12, 1999, Pages 2033-2035

Selective Epimerization of Rapamycin via a Retroaldol/Aldol Mechanism Mediated by Titanium Tetraisopropoxide

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; IMMUNOSUPPRESSIVE AGENT; RAPAMYCIN; TITANIUM; TITANIUM ISOPROPOXIDE;

EID: 0033576435     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991209o     Document Type: Article
Times cited : (23)

References (16)
  • 5
    • 0018831901 scopus 로고
    • Several numbering schemes are in use for rapamycin. We have opted to maintain the scheme previously employed by us (L.W.R.; D.A.H.) and originated by the group responsible for the structure elucidation of rapamycin. Findlay, J. A.; Radics, L. Can. J. Chem. 1980, 58, 579-590.
    • (1980) Can. J. Chem. , vol.58 , pp. 579-590
    • Findlay, J.A.1    Radics, L.2
  • 7
    • 0026697506 scopus 로고
    • 4 similarly and more rapidly yields its oxepane tautomer which reverts to pyran during chromatography (Wu Yang, unpublished). Hughes has reported the preparation and isolation of the oxepane tautomer of rapamycin: Hughes, P.; Musser, J.; Conklin, M.; Russo, R. Tetrahedron Lett. 1992, 33, 4739-4742. (Matrix Presented)
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4739-4742
    • Hughes, P.1    Musser, J.2    Conklin, M.3    Russo, R.4
  • 9
    • 0031025353 scopus 로고    scopus 로고
    • 4 has been utilized in macrolide total synthesis to facilitate ring size equilibration through transesterification; Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326-5351, Paterson, I.; Watson, C.; Yeung, K.-S.; Wallace, P. A.; Ward, R. A. J. Org. Chem. 1997, 62, 452-453.
    • (1997) J. Org. Chem. , vol.62 , pp. 452-453
    • Paterson, I.1    Watson, C.2    Yeung, K.-S.3    Wallace, P.A.4    Ward, R.A.5
  • 10
    • 84986984366 scopus 로고
    • 4 has been reported to promote intermolecular aldol condensation of enolizable aldehydes and ketones; however, the reactions are carried out at elevated temperatures and invariably result in dehydrated αβ unsaturated products. Mahrwald, R.; Schick, H. Synthesis 1990, 592-595.
    • (1990) Synthesis , pp. 592-595
    • Mahrwald, R.1    Schick, H.2
  • 12
    • 85088546966 scopus 로고
    • Ph.D. Dissertation, Yale University
    • 1H NMR of the 28.29-bisepirapamycin (4) we isolated was found to be consistent with that previously reported from the total synthesis. Hayward, C. M. Ph.D. Dissertation, Yale University, 1994.
    • (1994)
    • Hayward, C.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.