A new tandem route to angular tetraquinanes. Synthesis of the waihoensene ring system

Organic Letters

Volumn 1, Issue 3, 1999, Pages 375-377

  Ergüden, Jens Kerim ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; SYNTHESIS; X RAY DIFFRACTION;

INDENES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; X-RAY DIFFRACTION;

EID: 0033549668     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990023m     Document Type: Article

References (12)

1. MacDougall, J. M.; Moore, H. W. J. Org. Chem. 1997, 62, 4554.
2. MacDougall, J. M.; Santora, V. J.; Verma, S. K.; Trunbull, P.; Hernandez, C. R.; Moore, H. W. J. Org. Chem. 1998, 63, 6905.
3. Clarke, D. B.; Hinkley, S. F. R.; Weavers, R. T. Tetrahedron Lett. 1997, 38, 4297.
4. Xu, S. L.; Moore, H. W. J. Org. Chem. 1989, 54, 6018.
5. For examples see: Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. Paquette, L. A. Tetrahedron 1997, 53, 13971.
6. For examples see: Paquette, L. A. Eur. J. Org. Chem. 1998, 1709. Paquette, L. A. Tetrahedron 1997, 53, 13971.
7. Since a slight excess of the lithium reagent was used, workup under the aqueous conditions provides a basic reaction media.
8. This is in analogy to related oxy-Cope/transannular ring closures to polyquinanes staring with bicyclo[3.2.0]heptenones. See, for example: Santora, V. J.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486.
9. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375.
10. Utimoto, K.; Wakabayashi, Y.; Horiie, T.; Inoue, M.; Shishiyama, Y.; Obayashi, M.; Nozaki, H Tetrahedron 1983, 39, 973
11. Schlosser, M., Ed. Organometallics in Synthesis: a Mannual; Wiley: Chichester, West Sussex, England, New York, 1994.
12. Verma, S. Ph.D. Dissertation, University of California, Irvine, 1999.