Asymmetric synthesis of the tremulane skeleton by a tandem cyclopropanation/cope rearrangement

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 3967-3970

  Davies, Huw M L ^a   Doan, Brian D ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON; TETRAHYDROFURAN DERIVATIVE; TREMULANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029973850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00723-X     Document Type: Article

References (22)

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3. (c) Mann, J. Tetrahedron 1986, 42, 4611.
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9. (b) Davies, H. M. L.; Bruzinski, P.; Hutcheson, D. K.; Fall. M. J. J. Am. Chem. Soc., submitted
10. Davies, H. M. L.; Peng, Z. -Q.; Houser, J. H. Tetrahedron Lett. 1994, 35, 8939
11. (a) Ayer, W. A.; Cruz, E. R. J. Org. Chem. 1993, 58, 7529.
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13. For a recent synthesis of 8a-epi tremulenolide B, see Habeck, T.; Wolff, C.; Tochtermann, W. Tetrahedron Lett. 1995, 36, 2041.
14. Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 936.
15. (E,E)-2,4-Hexadien-1-ol is commercially available. (2Z,4E)-2,4-Hexadien-1-ol was prepared by sodium borohydride reduction of (2Z,4E)-2,4-Hexadienal, which was prepared according to: Furber, M.; Herbert, J. M.; Taylor, R. J. K. J. Chem. Soc., Perkin I, 1989, 683.
16. (a) Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709.
17. (b) Davies, H. M. L.; Cantrell, W. R., Jr.; Romines, K. R.; Baum, J. S. Org. Synth. 1991, 70, 93.
18. Davies, H. M. L.; McAfee, M. J.; Oldenburg, C. E. M. J. Org. Chem. 1989, 54, 930.
19. For the use of nOe analysis for stereochemical assignments of related compounds, see Ref. 10.
20. R = 15.2 min (major). The studies were carried out using the rhodium(II) (R)-prolinate catalyst 1 instead of the catalyst derived from the natural amino acid in order that the minor enantiomer of the product 9 eluted first during the HPLC analysis. The depicted absolute stereochemistry of the products is based on the assumption that the carbenoid face selectivity in these reactions is the opposite to that observed in the rhodium(II) (S)-prolinate catalyzed cyclopropanations described in Ref. 3
21. Davies, H. M. L.; Clark, T. J.; Smith, H. D. J. Org. Chem. 1991, 56, 3817.
22. Hudlicky, T.; Rulin, F.; Reed, J. W.; Gadamasetti, K. G. Org. Reacts. 1991, 41, 1.