Tandem Single-Step Construction of Chiral Hexahydrophenanthrenes: A Concise Route to (+)-Ferruginol

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1737-1740

  Nagata, Hiroshi ^a   Miyazawa, Norio ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABIETANE DERIVATIVE; DITERPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FERRUGINOL;

ALKYLATION; ARTICLE; PH; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; DITERPENES; DITERPENES, ABIETANE; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; STEREOISOMERISM;

EID: 0035979031     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015929i     Document Type: Article

References (19)

1. (a) Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds, Vol. II; Academic Press: New York, 1972; p 185.
2. (b) Hanson, J. R. Nat. Prod. Rep. 2000, 17, 165 and previous reports.
3. (a) Kametani, T. The Chemistry of the Isoquinoline Alkaloids, Vol. 2, Chapter 10; Kinkodo: Sendai, 1974.
4. (b) Bentley, K. W. Nat. Prod. Rep. 2001, 18, 148 and previous reports.
5. (a) Floyd, A. J.; Dyke, S. F.; Wards, S. E. Chem. Rev. 1976, 76, 509.
6. (b) Sutherland, J. K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Fleming, I., Ed.; Pergamon: Oxford, 1991; p 341.
7. Hawkins, R. T.; Hsu, R. S.; Wood, S. G. J. Org. Chem. 1978, 43, 4648.
8. Nagata, H.; Miyazawa, N.; Ogasawara, K. Synthesis 2000, 2013.
9. Ito, Y.; Fujii, S.; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. VI, p 327.
10. 1H NMR spectra after transformation into the (R)- and (S)-MTPA esters.
11. iPrOH-hexane 1:99 v/v).
12. Caine, D. Org. Prep. Proc. Int. 1988, 20, 1.
13. Birch, A. J.; Hill, J. S. J. Chem. Soc. C 1966, 419.
14. Yamada, O.; Ogasawara, K. Org. Lett. 2000, 2, 2785.
15. Tada, M.; Nishiiri, S.; Zhixiang, Y.; Imai, Y.; Tajima, S.; Okazaki, N.; Kitano, Y.; Chiba, K. J. Chem. Soc., Perkin Trans. 1 2000, 2657.
16. Brandt, C. W.; Neubauer, L. G. J. Chem. Soc. 1939, 1031.
17. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596.
18. Huang-Minlon, J. Am. Chem. Soc. 1949, 71, 3301.
19. Nagata, H.; Miyazawa, N.; Ogasawara, K. Chem. Commun., in press.