General approach for the synthesis of macroline/sarpagine related indole alkaloids via the asymmetric Pictet-Spengler reaction: The enantiospecific synthesis of (-)-anhydromacrosalhine-methine

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5033-5036

  Gan, Tong ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANHYDROMACROSALHINE METHINE; INDOLE ALKALOID; MACROLINE; PANDICINE; SARPAGINE; UNCLASSIFIED DRUG;

AMINO ACID METABOLISM; ARTICLE; DRUG SYNTHESIS; DYSENTERY; ENANTIOMER; ENTAMOEBA HISTOLYTICA; STEREOCHEMISTRY;

ENTAMOEBA HISTOLYTICA; STAPHYLOCOCCUS PHAGE 3A;

EID: 0030586109     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01009-X     Document Type: Article

References (17)

1. 1. Bi, Y.; Hamaker, L. K.; Cook, J. M. The Synthesis of Macroline Related Alkaloids. In Bioactive Natural Products, Part A; Basha, F. Z. and Rahman, A., Ed.; Elsevier Science: Amsterdam, 1993; Vol. 13; 383.
2. 2. Hamaker, L. K.; Cook, J. M. The Synthesis of Macroline Related Sarpagine Alkaloids. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Elsevier Science: New York, 1995; Vol. 9; 23.
3. 3. Wright, C. W.; Allen, D.; Cai, Y.; Phillipson, J. D.; Said, I. M.; Kirby, G. C.; Warhurst, D. C. Phytother. Res. 1992, 6, 121.
4. 4. Ghedira, K.; Zeches-Hanrot, M.; Richard, B.; Massiot, G.; LeMen-Oliver, L.; Sevenet, T.; Goh, S. H. Phytochemistry 1988, 27, 3955.
5. 5. Khan, Z. M.; Hesse, M.; Schmid, H. Helv. Chim. Acta 1967, 50, 1002.
6. 6. Mayerl, F.; Hesse, M. Helv. Chim. Acta 1978, 61, 337.
7. 7. Kan-Fan, C.; Massiot, G.; Das, B. C.; Potier, P. J. Org. Chem. 1981, 46, 1481.
8. 8. Zhang, L. H.; Cook, J. M. J. Am. Chem. Soc. 1990, 112, 4088.
9. 9. Fu, X.; Cook, J. M. J. Am. Chem. Soc. 1992, 114, 6910.
10. 10. Bi, Y.; Zhang, L. H.; Hamaker, L. K.; Cook, J. M. J. Am. Chem. Soc. 1994, 116, 9027.
11. 11. Takayama, H.; Phisalaphong, C.; Kitajima, M.; Aimi, N.; Sakai, S. Tetrahedron 1991, 47, 1383.
12. 12. Kishi, T.; Hesse, M.; Gemenden, C. W.; Taylor, W. I.; Schmid, H. Helv. Chim. Acta 1965, 48, 1349.
13. 13. Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704.
14. 14. Reich, H. J.; Wollowitz, S. J. Am. Chem. Soc. 1982, 104, 7051.
15. 15. Zhang, L. H.; Bi, Y.; Yu, F.; Menzia, G.; Cook, J. M. Heterocycles 1992, 34, 517.
16. 16. The Claisen rearrangement in the 11-methoxy series 17 provided the desired β-dicarbonyl compound 18 in 76% yield. See Hamaker, L. K. Ph.D. Thesis, University of Wisconsin-Milwaukee, 1995. (equation presented)
17. 17. Zhang, P.; Cook, J. M. Syn. Comm. 1995, 25, 3883.