Construction of the pentacyclic ring system of apogeissoschizine

Tetrahedron

Volumn 52, Issue 25, 1996, Pages 8601-8610

  Bennasar, M Lluïsa ^a   Zulaica, Ester ^a   Sufi, Bilal A ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GEISSOSCHIZINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0030014155     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00400-0     Document Type: Article

References (17)

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3. The biogenetic numbering is used throughout this paper for tetracyclic and pentacyclic compounds. Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508-510.
4. Quetin-Leclercq, J.; Dive, G.; Delaude, C.; Warin, R.; Bassleer, R.; Angenot, L. Phytochemistry 1994, 35, 533-536.
5. For a recent review on the nucleophilic addition of indole-containing enolates to pyridinium salts, see: Bennasar, M-L.; Bosch, J. Synlett 1995, 587-596.
6. This strategy has been successfully used in the synthesis of 2,7-dihydropleiocarpamine, an alkaloid of the C-mavacurine group: Bennasar, M.-L.; Zulaica, E.; Jiménez, J.-M.; Bosch, J. J. Org. Chem. 1993, 58, 7756-7767.
7. For the use of this procedure in the synthesis of (E)-ethylidene bearing indole alkaloids, see: (a) Besselièvre, R.; Cosson, J.-P.; Das, B. C.; Husson, H.-P. Tetrahedron Lett. 1980, 21, 63-66.
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9. (a) Trost, B. M.; Murayama, E. J. Am. Chem. Soc. 1981, 103, 6529-6530.
10. (b) Trost, B. M.; Sato, T. J. Am. Chem. Soc. 1985, 707, 719-721.
11. (c) For DMTSF-induced cyclizations upon the indole 3-position, see: Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299-6312. See also reference 6.
12. (a) Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750-4757.
13. (b) Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792-5796.
14. (c) Catena, J. L.; Valls, N.; Bosch, J.; Bonjoch, J. Tetrahedron Lett. 1994, 35, 4433-4436.
15. For the formation of dithioacetals from sulfoxides under Pummerer reaction conditions, see: Harris, T. D.; Boekelheide, V. J. Org. Chem. 1976, 41, 2770-2772.
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