Cascade rearrangement of 5-cyclopentylidenecyclooctanones

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 2972-2979

  Kakiuchi, Kiyomi ^a   Okada, Hideki ^a   Kanehisa, Nobuko ^a   Kai, Yasushi ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038322542     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519017     Document Type: Article

References (27)

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2. (b) Gange, D.; Magnus, P.; Bass, L.; Arnold, E. V.; Clardy, A. J. J. Am. Chem. Soc. 1980, 102, 2134 and references cited therein.
3. The terms primary, secondary, and tertiary structure are used for classification of macromolecular structures and are briefly described as follows: primary, the structural formula of the monomer units, including bond length and bond angles, and leading to the resultant special geometry of the macromolecules; secondary, the manner in which monomer units are folded to generate simple structures, and nearly every secondary structure is helical; tertiary, the relative arrangement of the secondary structure(s), resulting from small periodic variations or the chain folding in secondary structure. For more extensive discussion, see: Hopfinger, A. J. Conformational Properties of Macromolecules; Academic Press: New York, 1973.
4. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701; 1993, 115, 9421
5. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701; 1993, 115, 9421
6. Kakiuchi, K.; Fukunaga, K.; Matsuo, F.; Ohnishi, Y.; Tobe, Y. J. Org. Chem. 1991, 56, 6742.
7. See the supplementary material in ref 4.
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13. Roush, W. R.; Gillis, H. R.; Essenfeld, A. P. J. Org. Chem. 1984, 49, 4674
14. For example, the chemical shifts of the bridgehead quaternary carbon having a hydroxyl group are 87.06 and 89.97 ppm for diquinane and angularly fused triquinane-type compounds; see: Kakiuchi, K.; Tsugaru, T.; Takeda, M.; Wakaki, I.; Tobe, Y.; Odaira, Y. J. Org. Chem. 1985, 50, 488.
15. Allinger, N. L. QCPE No. MM2 (85). Also, calculations were performed with the MM2 program using an Iris Indigo R4000 computer. The output was recorded by using MOL-GRAPH program Ver. 2.8 by Daikin Industries, Ltd.
16. 4 did not give the ketone 11a, and the starting material was recovered.
17. Cargill, R. L.; Dalton, J. R.; O'Connor, S.; Michels, D. G. Tetrahedron Lett. 1978, 4465.
18. Lambert, J. B.; Clikeman, R. R. J. Am. Chem. Soc. 1976, 98, 4203. Kakiuchi, K.; Ue, M.; Tsukahara, H.; Simizu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707.
19. Lambert, J. B.; Clikeman, R. R. J. Am. Chem. Soc. 1976, 98, 4203. Kakiuchi, K.; Ue, M.; Tsukahara, H.; Simizu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707.
20. The NMR data of 25 showed similarity to those of 30 and 31 which have bis-propellane-type tetrahydrofuran structures; see the Experimental Section and the supporting information.
21. Allen, F.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1 (supplement).
22. 3, which is reported to be a useful method for synthesis of tertiary chloride from the corresponding tertiary alcohols under extremely mild conditions; see: Carman, R. H.; Shaw, I. M. Aust. J. Chem. 1976, 29, 133. While some products including a small amount of 29 were detected by GLC analysis, we did not characterize them.
23. 13 to be -59.68, -70.42, and -67.74 kcal/mol, respectively.
24. McMurry, J. E.; Haley, G. J.; Matz, J. R.; Clardy, J. C.; Van Duyne, G.; Gleiter, R.; Schäfer, W.; White, D. H. J. Am. Chem. Soc. 1986, 108, 2932.
25. Hoogesteger, F. J.; Havenith, R. W. A.; Zwikker, J. W.; Jenneskens, L. W.; Kooijman, H.; Veldman, N.; Spek, A. L. J. Org. Chem. 1995, 60, 4375 and references cited therein.
26. teXsan: Crystal Structure Analysis Package, Molecular Structure Corp. (1985 and 1992).
27. The author has deposited atomic coordinates for 25 and 29 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.