Synthesis of bicyclic analogues of dehydroilludin M

Synthetic Communications

Volumn 27, Issue 3, 1997, Pages 521-532

  Kinder Jr , Frederick R ^a   Wang, Run Ming ^a   Bauta, William E ^a   Bair, Kenneth W ^a  

^a Sandoz Pharma Ltd   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; ILLUDIN DERIVATIVE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 1842369096     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006054     Document Type: Article

References (10)

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2. McMorris, T.C. and Anchel, M. J. Am. Chem. Soc. 1963, 85, 831.
3. Nakanishi, K.; Ohashi, M.; Tada, M.; Yamada, Y. Tetrahedron 1965, 21, 1231.
4. Matsumoto, T., Shirahama, H., Ichihara, A., Tukuoka, Y. and Takahashi, Y.; Mori, Y.; Watanabe, M. Tetrahedron 1965, 21, 2671.
5. Kelner, M.J., McMorris, T.C. and Taetle, R. J. Natl. Cancer Inst. 1990, 82, 1562.
6. McMorris, T.C., Keiner, M.J., Wang, W., Estes, L.A., Montoya, M.A. and Taetle, R. J.Org.Chem. 1992, 57, 6876.
7. 1′ alkylation of the cyclopropane ring by a DNA nucleophile. Delocalization of electrons toward the incipient carbocation is expected to be much slower for dehydroilludin M compared to illudin M.
8. Padwa, A., Chinn, R.L., Hornbuckle, S.F. and Zhang, Z.J. J. Org. Chem. 1991, 56, 3271.
9. Kinder, F.R. and Bair, K.W. J. Org. Chem. 1994, 59, 6965.
10. This material was prepared from tetrahydro-2-(3-butynyloxy)-2H-pyran in the same manner as reported by Earl, R.A. and Townsend, L.B. Org. Synth. 1981, 60, 81.