General approach for the synthesis of macroline/sarpagine related indole alkaloids via the asymmetric Pictet-Spengler reaction: The enantiospecific synthesis of the N(a)-H, azabicyclo[3.3.1]nonone template

Tetrahedron Letters

Volumn 38, Issue 39, 1997, Pages 6819-6822

  Yu, Peng ^a   Wang, Tao ^a   Yu, Fuxiang ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.3.1]NONANE DERIVATIVE; HETEROCYCLIC KETONE; INDOLE ALKALOID; TRYPTOPHAN;

ARTICLE; CIS TRANS ISOMERISM; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030848010     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01603-1     Document Type: Article

References (11)

1. Bi, Y.; Hamaker, L. H. and Cook, J. M. "The Synthesis of Macroline Related Alkaloids," in Studies in Natural Products Chemistry, Bioactive Natural Products, Part A, Vol. 13, Atta-ur-Rahman, A. and Basha, F. (eds.), Elsevier, Amsterdam, 1993, p. 383.
2. Hamaker, L. H. Ph.D. Thesis, University of Wisconson - Milwaukee, Milwaukee, WI, 1995.
3. a) Hamaker, L. H. and 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; p 23.
4. b) Bi, Y.; Zhang, L. H.; Hamaker, L. H. and Cook, J. M. " J. Am.Chem Soc. 1994, 116, 9027.
5. c) Fu, X. and Cook, J. M. J. Am. Chem. Soc. 1992, 114, 6901.
6. Magnus, P.; Mugrage, B.; Deluca, M. R. and Cain, G. A. J. Am. Chem. Soc. 1990, 112, 5220.
7. Bailey, P. D. and McLay, N. R. Tetrahedron Lett. 1991, 31, 3895.
8. Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W. and Cook, J. M. J. Org.Chem. 1997, 62, 44.
9. Hobson, J. D.; Raines, J. and Whiteoak, R. J. J. Chem. Soc. 1963, 3495.
10. Shimizu, Masato; Ishikawa, Masayuki; Komoda, Yasuo; Nakajima, Terumi; Yamaguchi, Keiichi and Sakai, Shin-ichiro Chem. Pharm. Bull. 1984 , 32, 1313.
11. Cain, M.; Campos, O.; Guzman, F. and Cook, J. M. J. Am. Chem. Soc. 1983, 105, 907.