Asymmetric synthesis of the pentacyclic ring system of aspidosperma alkaloids

Tetrahedron

Volumn 53, Issue 42, 1997, Pages 14247-14254

  Okada, Kunisuke ^a   Murakami, Kazumasa ^a   Tanino, Hideo ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ASPIDOSPERMINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

ASPIDOSPERMA; STAPHYLOCOCCUS PHAGE 3A;

EID: 0030815127     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00992-7     Document Type: Article

References (13)

1. Node, M.; Nagasawa, H.; Fuji, K. J. Am. Chem. Soc. 1987, 109, 7901-7903. Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521.
2. Node, M.; Nagasawa, H.; Fuji, K. J. Am. Chem. Soc. 1987, 109, 7901-7903. Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521.
3. Ihara, M.; Yasui, K.; Taniguchi, N.; Fukumoto, K. Heterocycles, 1990, 31, 1017-1020. Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Niitsuma, H.; Fukumoto, K. J. Chem. Soc. Perkin Trans. 1, 1991, 525-535.
4. Ihara, M.; Yasui, K.; Taniguchi, N.; Fukumoto, K. Heterocycles, 1990, 31, 1017-1020. Ihara, M.; Takahashi, M.; Taniguchi, N.; Yasui, K.; Niitsuma, H.; Fukumoto, K. J. Chem. Soc. Perkin Trans. 1, 1991, 525-535.
5. Okada, K.; Katsura, T.; Tanino, H.; Kakoi, H.; Inoue, S. Chemistry Lett. 1994, 157-160. Okada, K.; Murakami, M.; Tanino, H.; Kakoi, H.; Inoue, S. Heterocycles, 1996, 43, 1735-1750 and see ref.4.
6. Okada, K.; Katsura, T.; Tanino, H.; Kakoi, H.; Inoue, S. Chemistry Lett. 1994, 157-160. Okada, K.; Murakami, M.; Tanino, H.; Kakoi, H.; Inoue, S. Heterocycles, 1996, 43, 1735-1750 and see ref.4.
7. Seki, K.; Ohnuma, T.; Oishi, T.; Ban, Y. Tetrahedron Lett. 1975, 723-726. Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T. J. Am. Chem. Soc. 1981, 103, 6990-6992. Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron, 1983, 39, 3657-3668.
8. Seki, K.; Ohnuma, T.; Oishi, T.; Ban, Y. Tetrahedron Lett. 1975, 723-726. Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T. J. Am. Chem. Soc. 1981, 103, 6990-6992. Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron, 1983, 39, 3657-3668.
9. Seki, K.; Ohnuma, T.; Oishi, T.; Ban, Y. Tetrahedron Lett. 1975, 723-726. Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T. J. Am. Chem. Soc. 1981, 103, 6990-6992. Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron, 1983, 39, 3657-3668.
10. For the other asymmetric synthesis of aspidospermidine, see: Desmae"le, D.; d'Angelo, J. J. Org. Chem., 1994, 59, 2292-2303.
11. Enantiomeric enrichment of 11 a∼d might be performed at this stage.
12. 3)} obtained from 11a was similar to that of 12 obtained from 11d. Conversion of 11a into 12 in acidic condition should proceed, without loss of the chirality at C5, as follows: 1) aldol type condensation-dehydration, 2) cleavage of C12-C19 bond promoted by protonation to the α,β-unsaturated carbonyl group and 3) recyclization through stable transition state.
13. Recently, similar acid-catalized cyclization was reported: Mirand, C.; Papa, M.; Cartier, D.; Le'vy, J. Tetrahedron Lett., 1997, 38, 2263-2266 and references cited therein.