Construction of the tricyclo[5.3.1.01,5]undecane system by a tandem pinacol rearrangement-ene strategy: A formal synthesis of (±)-perhydrohistrionicotoxin

Chemical Communications

Volumn , Issue 23, 1997, Pages 2263-2264

  Kim, Deukjoon ^a   Hong, Sung Woo ^a   Park, Cheol Won ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007322358     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a706193e     Document Type: Article

References (9)

1. Y. Chen and W. Lin, Tetrahedron Lett., 1992, 33, 1749 and references cited therein.
2. Pinacol rearrangement of a Diels-Alder derived bicyclo[2.2.2]octene 2 has previously been exploited in the synthesis of various natural products: (a) S. A. Monti, S. Chen, Y. Yang, S. Yuan and O. P. Bourgeois, J. Org. Chem., 1978, 43, 4062;
3. (b) S. A. Monti and T. R. Dean, J. Org. Chem., 1982, 47, 2679 and references cited therein.
4. T. Ibuka, Y. Mitsui, K. Hayashi, H. Minakata and Y. Inubushi, Tetrahedron Lett., 1981, 22, 4425;
5. E. R. Koft and A. B. Smith, III, J. Org. Chem., 1984, 49, 832.
6. E. J. Corey, J. F. Arnett and G. N. Widiger, J. Am. Chem. Soc., 1975, 97, 430 and references cited therein.
7. A. Greiner, Tetrahedron Lett., 1989, 30, 3547.
8. Baeyer-Villiger reaction of the deoxy ketone 10′, prepared from 10 by elimination and catalytic hydrogenation, produced the desired lactone 13 and its regioisomeric lactone in a 5 : 1 ratio: T. Ho, in Polarity Control for Synthesis, Wiley, New York, 1991, p. 353.
9. F. A. Davis, L. C. Vishwaskarma, J. M. Billmers and J. Finn, J. Org. Chem., 1984, 49, 3241.