Synthesis of angularly-fused benzocyclobutenedione monoketals: Useful synthetic intermediates to angucyclines

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2170-2171

  Tiedemann, Ralf ^a   Heileman, Matthew J ^a   Moore, Harold W ^a   Schaumann, Ernst ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0033515606     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982422l     Document Type: Article

References (19)

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3. For an elegant application of this electrocyclic cascade in natural products synthesis, see: Nicolaou, K. C.; Petasis, N. A.; Zipin, R. E.; Uenishi, J. J. Am. Chem. Soc. 1982, 104, 5555.
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5. For a recent review on these compounds, see: Rohr, J.; Thiericke, R. Natural Prod. Rep. 1992, 103. Also see: (a) Krohn, K.; Ballwanz, F.; Baltus, W. Liebigs Ann. Chem. 1993, 911.
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14. For examples of analogous synthetic methodology, see: (a) Gayo, L.; Moore, H. W. J. Org. Chem. 1992, 57, 6896.
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16. Denmark, S. E.; Hite, G. A. Helv. Chim. Acta 1988, 71, 195. A better yield of 1-bromo-2-ethenylcyclohexene can be obtained by doing a Peterson instead of a Wittig olefination. Specifically, treatment of 2-bromo-1-cyclohexene-1-carbaldehyde with trimethylsilylmethyllithium followed by acidic workup (concentrated HCl) furnished the bromodiene in 80% yield.
17. 4 and zinc powder. For a similar procedure, see: Coe, P. L.; Scriven, C. E. J. Chem. Soc., Perkin Trans. 1 1986, 475.
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