Absolute configuration of macrocyclic spermidine alkaloids

Chirality

Volumn 9, Issue 5-6, 1997, Pages 523-528

  Schultz, Katja ^a   Kuehne, Paul ^a   Häusermann, Ursula A ^a   Hesse, Manfred ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Absolute configuration; Biogenesis; Macrocyclic spermidine alkaloids; Stereochemistry; Stereoselective synthesis

Indexed keywords

ALKALOID; CELAFURINE; MACROCYCLIC COMPOUND; NATURAL PRODUCT; SPERMIDINE DERIVATIVE; UNCLASSIFIED DRUG; VIBURNINE;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ORGANIC CHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030929557     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<523::AID-CHIR19>3.0.CO;2-Q     Document Type: Article

References (24)

1. (a) Guggisberg, A., Hesse, M. Putrescine, spermidine, spermine and related polyamine alkaloids. In: The Alkaloids. Brossi, A. ed. New York: Academic Press Inc., 1983:85-188, and references cited therein.
2. (b) Wagner, H., Burghart, J. Spermidine alkaloids and triterpenes from Maytenus heterophylla and Pleurostylia africana. Planta Medica 32a:9-14, 1977.
3. (c) Wagner, H., Burghart, J., Bladt, S. Pleurostylin, ein neues macrocyclisches Spermidinalkaloid aus Pleurostylia africana Loes. Tetrahedron Lett. 9:781-782, 1978.
4. (d) Séguineau, C., Richhomme, P., Bruneton, J., Pusset, J. New hydroxylated spermidine alkaloids from Pleurostylia opposita (Wall.) Merill-Metcalf. Helv. Chim. Acta 75:2283-2288, 1992.
5. (e) Séguineau, C., Richhomme, P., Bruneton, J. 7-Hydroxypleucorine, a new alkaloid isolated from Pleurostylia opposita. Heterocycles 38:181-187, 1994.
6. (f) Abdallah, O.M., Ibraheim, Z.Z. Viburnine, a macrocyclic spermidine alkaloid from Viburnum rhytidophyllum. Bull. Pharm. Sci. 18:39-43, 1995.
7. Kupchan, S.M., Hintz, H.P.J., Smith, R.M., Karim, A., Cass, M.W., Court, W.A., Yatagai, M. Macrocyclic spermidine alkaloids from Maytenus serrata and Tripterygium wilfordii. J. Org. Chem. 42:3660-3664, 1977.
8. Iida, H., Fukuhara, K., Machiba, M., Kikuchi, T. Total synthesis of (-)-dihydrocelacinnine and (±)-celabenzine. Tetrahedron. 27:207-210, 1986.
9. Hoquemiller, R., Cavé, A., Husson, H.-P. Alkaloids du Peripterygia marginata (Baill.) Loes. (Celastraceae) I and II. Tetrahedron Lett. 33:645-656, 1977.
10. (a) Kaseda, T., Kikuchi, T., Kibayashi, C. Enantioselective total synthesis of (+)-(S)-dihydroperiphylline. Tetrahedron Lett. 30:4539-4542, 1989.
11. (b) Isihara, K., Kuroki Y., Yamamoto, H. A concise synthesis of (+)-(S)-dihydroperiphylline. Synlett: 41-42, 1995.
12. (a) Lotter, H.L., Abraham, D.J., Turner, C.E., Knapp, J.E., Schiff, P.L., Slatkin, D.J. Cannabisativine, a new alkaloid from Cannabis sativa L. root. Tetrahedron Lett. 33:2815-2818, 1975.
13. (b) Turner, C.E., Hsu, M.-F.H., Knapp, J.E., Schiff, P.L., Slatkin, D.J. Isolation of cannabisativine, an alkaloid from Cannabis sativa L. root. J. Pharm. Sci. 65:1084-1085, 1976.
14. Hamada, T., Zenkoh, T., Sato, H., Yonemitsu, O. A chiral synthesis of (-)-cannabisativine: An application of the highly diastereoselective hetero Diels-Alder reaction. Tetrahedron Lett. 32:1649-1652, 1991.
15. Díaz, M., Preiss, A., Ripperger, H. Loesenerine, an alkaloid from Maytenus loeseneri. Phytochemistry 26:1847-1848, 1987.
16. Preiss, A., Diaz, M., Ripperger, H. 17,18-Didehydroloesenerine and 16,17-didehydroloesenerin-18-ole, alkaloids from Maytenus loeseneri. Phytochemistry 27:589-593, 1988.
17. Bashwira, S., Hootele, C. Myricoidine and dihydromyricoidine, two new macrocyclic spermidine alkaloids from Clerodendrum myricoides. Tetrahedron. 44:4521-4526, 1988.
18. Häusermann, U.A., Linden, A., Song, J., Hesse, M. Helv. Chim. Acta 79:1995-2003, 1996.
19. Kuehne, P., Linden, A., Hesse, M. Asymmetric synthesis of the alkaloids mayfoline and N(1)-acetyl-N(1)-deoxymayfoline. Helv. Chim. Acta 79:1085-1093, 1996.
20. Schultz, K., Hesse, M. Total synthesis of (+)-(8S,13R)-cyclocelabenzine. Helv. Chim. Acta 79:1295-1304, 1996.
21. Schultz, K., Hesse, M. Total synthesis of the spermidine alkaloid (+)-(9S,13S)-isocyclocelabenzine, Tetrahedron 52:14247-14254, 1997.
22. Ito, N., Matsuyama, H., Yoshida, M., Kamigata, N., Iyoda, M. Asymmetric synthesis of celacinnine utilizing optically active vinyl sulfoxides. Heterocycles 41:415-418, 1995.
23. 3) is most probably due to a part protonation by HCl of our compound.
24. Christen, H.R., Vögtle, F. In: Grundlagen der Organischen Chemie. Salle, Frankfurt/Main: Sauerländer Aarau 1989:301-310.