Synthesis of rac-midpacamide and the spiro-cyclization of its precursor

Liebigs Annales

Volumn , Issue 7, 1997, Pages 1525-1528

  Lindel, Thomas ^a   Hoffmann, Holger ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkaloids; Biomimetic synthesis; Marine sponges; Natural products; Spiro cyclization

Indexed keywords

EID: 33748819378     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970731     Document Type: Article

References (24)

1. D. H. Attaway, O. R. Zaborsky (Eds.), Marine Biotechnology, vol. 1, Plenum Press, New York, 1993.
2. [2a] S. Forenza, L. Minale, R. Riccio, E. Fattorusso, J. Chem. Soc., Chem. Commun. 1971, 1129-1130.
3. [2b] E. E. Garcia, L. E. Benjamin, R. I. Fryer, J. Chem. Soc., Chem. Commun. 1973, 78-79.
4. For a recent review see: [3a] G. W. Gribble in Fortschr. Chem. Org. Naturst., vol. 68 (Eds.: W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, C. Tamm), Springer, Wien, 1996, p. 137ff.
5. [3b] M. D'Ambrosio, A. Guerriero, M. Ripamonti, C. Debitus, J. Waikedre, F. Pietra, Helv Chim. Acta 1996, 79, 727-735.
6. [3c] R. B. Kinnel, H.-P. Gehrken, P. J. Scheuer, J. Am. Chem. Soc. 1993, 115, 3376-3377.
7. [3d] F. Cafieri, E. Fattorusso, A. Mangoni, O. Taglialatela-Scafati, Tetrahedron Lett. 1996, 37, 3587-3590.
8. [3e] D. H. Williams, D. J. Faulkner, Tetrahedron 1996, 52, 5381-5390.
9. [3f] S. Tsukamoto, H. Kato, H. Hirota, N. Fusetani, J. Nat. Prod. 1996, 59, 501-503.
10. F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437-2488;
11. Angew. Chem. Int. Ed. Engl. 1996, 108, 2288-2337.
12. [5a] G. M. sharma, P. R. Burkholder, J. Chem. Soc., Chem. Commun. 1971, 151-152.
13. [5b] G. M. Sharma, B. Magdoff-Fairchild, J. Org. Chem. 1977, 42, 4118-4124.
14. L. H. Foley, G. Büchi, J. Am. Chem. Soc. 1982, 104, 1776-1777.
15. D. M. Bailey, R. E. Johnson, J. Med. Chem. 1973, 16, 1300-1302.
16. Y. Xu, K. Yakushijin, D. A. Horne, J. Org. Chem. 1997, 62, 456-464.
17. E. Ware, Chem. Rev. 1950, 46, 403-470 and ref. cited therein.
18. N. A. Meanwell, H. R. Roth, E. C. R. Smith, D. L. Wedding, J. J. K. Wright, J. Org. Chem. 1991, 56, 6897-6904.
19. Dialkylated β-aminopropionic aldehydes are known to be hydrolyzed under mild basic conditions: T. Fukuyama, F. Nakatsubo, A. J. Cocuzza, Y. Kishi, Tetrahedron Lett. 1977, 18, 4295-4298.
20. [12a] L. Chevolot, S. Padua, B. N. Ravi, P. C. Blyth, P. Scheuer, Heterocycles 1977, 7, 891-894.
21. [12b] R. Fathi-Afshar, T. M. Allen, Can. J. Chem. 1988, 66, 45-50.
22. [12cl C. Jiménez, P. Crews, Tetrahedron Lett. 199-1, 35, 1375-1378. Natural midpacamide is probably racemic. No optical rotation has ever been reported.
23. Such selectivity is usually difficult to achieve: H.-J. Rimek, Methoden Org. Chem. (Houben-Weyl) 4th ed., 1980, vol. 4/lc, p. 155f.
24. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd ed., Pergamon, Oxford, 1988.