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Volumn , Issue 11, 1998, Pages 2483-2492

Exploration of high-pressure cycloadducts of furans and citraconic anhydride as precursors for CD-ring fragments of paclitaxel and its analogues

Author keywords

Ether cleavage in 7 oxabicyclo 2.2.1 heptanes; Furan cycloadditions; High pressure Diels Alder reactions; Paclitaxel (Taxol ); Paclitaxel CD ring

Indexed keywords


EID: 0002373813     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199811)1998:11<2483::AID-EJOC2483>3.0.CO;2-M     Document Type: Article
Times cited : (17)

References (44)
  • 10
    • 2842515322 scopus 로고    scopus 로고
    • note
    • The reaction can also be performed at pressures as low as 8 kbar. In order to reduce the reaction times, however, all high-pressure reactions were performed at 15 kbar.
  • 11
    • 2842594349 scopus 로고    scopus 로고
    • note
    • Conversion was monitored by NMR and determined by integrating the signal of the methyl group of citraconic anhydride and those of the 2- and 6-methyl groups of the two products.
  • 12
    • 2842555430 scopus 로고    scopus 로고
    • note
    • The furan cycloadducts return to their starting materials within a few days upon standing in solution at room temperature and within a few hours upon heating to 50°C.
  • 14
    • 0003625321 scopus 로고
    • Oak Ridge National Laboratory, Tennessee, USA
    • [12b] C. K. Johnson, ORTEP Report ORNL-3789, Oak Ridge National Laboratory, Tennessee, USA, 1965.
    • (1965) ORTEP Report ORNL-3789
    • Johnson, C.K.1
  • 15
    • 0001216681 scopus 로고
    • One of the referees brought to our attention that this steric interaction can also be explained by application of Newman's "rule of 6". In the unreactive anhydride the carbonyl oxygen atom is six atoms apart from the H atoms on the 1-methyl group. See also: M. S. Newman, J. Am. Chem. Soc. 1950, 72, 4783.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 4783
    • Newman, M.S.1
  • 44
    • 2842612092 scopus 로고    scopus 로고
    • note
    • 1H-NMR spectra of compounds 6a and 6b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.