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Volumn 53, Issue 32, 1997, Pages 11153-11170

A convergent synthesis of (+)-pancratistatin based on intramolecular electrophilic aromatic substitution

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PANCRATISTATIN; UNCLASSIFIED DRUG;

EID: 0030851951     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00373-6     Document Type: Article
Times cited : (78)

References (65)
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    • Chemical Information, National Institutes of Health
    • NCI Investigational Drugs. Chemical Information, National Institutes of Health, 1988, pp. 273-275.
    • (1988) NCI Investigational Drugs , pp. 273-275
  • 15
    • 0343095741 scopus 로고    scopus 로고
    • Natural Products Branch, NCI, Frederick Cancer Research and Development Center (personal communication)
    • Dr. Gordon M. Cragg, Natural Products Branch, NCI, Frederick Cancer Research and Development Center (personal communication).
    • Cragg, G.M.1
  • 29
    • 0019952166 scopus 로고
    • (b) Paulsen, H.; Stubbe, M. Tetrahedron Lett. 1982, 23, 3171-3174; Liebig's Ann. Chem. 1983, 535-556.
    • (1983) Liebig's Ann. Chem. , pp. 535-556
  • 31
    • 0025837981 scopus 로고
    • Others have described convergent syntheses of (+)-lycoricidine (3). Each of these syntheses have united aromatic and cyclitol components by an intramolecular Heck coupling. See: (a) Chida, N.; Ohtsuka, M.; Ogawa, S. Tetrahedron Lett. 1991, 32, 4525-4528; J. Org. Chem. 1993, 55, 4441-4447.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4525-4528
    • Chida, N.1    Ohtsuka, M.2    Ogawa, S.3
  • 32
    • 0025837981 scopus 로고
    • Others have described convergent syntheses of (+)-lycoricidine (3). Each of these syntheses have united aromatic and cyclitol components by an intramolecular Heck coupling. See: (a) Chida, N.; Ohtsuka, M.; Ogawa, S. Tetrahedron Lett. 1991, 32, 4525-4528; J. Org. Chem. 1993, 55, 4441-4447.
    • (1993) J. Org. Chem. , vol.55 , pp. 4441-4447
  • 40
    • 37049057209 scopus 로고
    • We were unable to reproduce the bis-acetonation of epi-inositol following the procedure of Angyal and Gilham. See Angyal, S. J.; Gilham, P. T. J. Chem. Soc. 1958, 375-379.
    • (1958) J. Chem. Soc. , pp. 375-379
    • Angyal, S.J.1    Gilham, P.T.2
  • 55
    • 0004159850 scopus 로고
    • McGraw-Hill: New York.
    • A similar influence operates in the solvolysis of alkoxymethyl halides. See: (a) Streitweiser, A. Jr. Solvolytic Displacement Reactions; McGraw-Hill: New York. 1962; pp. 102-103.
    • (1962) Solvolytic Displacement Reactions , pp. 102-103
    • Streitweiser A., Jr.1
  • 56
    • 0001139778 scopus 로고
    • Another analogy can be found in the rearrangement of 3,3-disubstituted indolenines to 2,3-disubstituted indoles. The migrations involved here can be directed by oxygen or nitrogen. See: (b) Jackson, A. H.; Smith, A. E. Tetrahedron 1968, 24, 403-413.
    • (1968) Tetrahedron , vol.24 , pp. 403-413
    • Jackson, A.H.1    Smith, A.E.2
  • 59
    • 0343531670 scopus 로고    scopus 로고
    • note
    • Pentacycle 19 was prepared alternatively by the benzylation of phenol 38 derived by metal/halogen exchange performed on 33.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.