Intramolecular cationic [5 + 2] cycloaddition reactions promoted by trimethylsilyl triflate in 3.0 M lithium perchlorate-ethyl acetate: Application to a formal total synthesis of (±)-isocomene

Tetrahedron

Volumn 53, Issue 26, 1997, Pages 8975-8996

  Grieco, Paul A ^a   Walker, John K ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; BENZOQUINONE; LITHIUM PERCHLORATE; QUINONE DERIVATIVE; TRIMETHYLSILYL TRIFLATE; TRIQUINANE ISOCOMENE; UNCLASSIFIED DRUG;

ACETYLATION; ALKYLATION; ARTICLE; CATALYSIS; DRUG ISOLATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL;

EID: 0030855201     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00581-4     Document Type: Article

References (23)

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8. For heteroatom variants of the cationic [5 + 2] cycloaddition process see: Garst, M.E.; McBride, B. J.; Douglass, J.G. Tetrahedron Lett. 1983, 24, 1675. Hendrickson, J.B.; Farina, J.S. J. Org. Chem. 1980, 45, 3359. Sammes, P.G.; Street, L.J. J. Chem. Soc. Perkin Trans.1 1983, 1261. Wender, P.A.; Mascareñas, J.L. Tetrahedron Lett. 1992, 33, 2115. Sammes, P.G.; Street, L.J. J. Chem. Soc., Chem. Commun. 1982, 1056. Wender, P.A.; McDonald, F.E. J. Am. Chem. Soc. 1990, 112, 4956.
9. For heteroatom variants of the cationic [5 + 2] cycloaddition process see: Garst, M.E.; McBride, B. J.; Douglass, J.G. Tetrahedron Lett. 1983, 24, 1675. Hendrickson, J.B.; Farina, J.S. J. Org. Chem. 1980, 45, 3359. Sammes, P.G.; Street, L.J. J. Chem. Soc. Perkin Trans.1 1983, 1261. Wender, P.A.; Mascareñas, J.L. Tetrahedron Lett. 1992, 33, 2115. Sammes, P.G.; Street, L.J. J. Chem. Soc., Chem. Commun. 1982, 1056. Wender, P.A.; McDonald, F.E. J. Am. Chem. Soc. 1990, 112, 4956.
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