Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

Chirality

Volumn 12, Issue 5-6, 2000, Pages 400-403

  Ohori, Ken ^a   Shimizu, Satoshi ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Catalytic asymmetric Michael addition; Catalytic asymmetric synthesis; Strychnos alkaloids

Indexed keywords

19,20 DIHYDROAKUAMMICINE; AKUAMMICINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COLUMN CHROMATOGRAPHY; COMPLEX FORMATION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0034034225     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h     Document Type: Article

References (30)

1. Bosch J, Bonjoch J, Amot M. Reviews for pentacylic indole alkaloids. In: Cordell GA, editor. The alkaloids, vol. 48. New York: Academic Press; 1996. p 75-189.
2. a) Kuehene ME, Xu F. Total synthesis of (±)-strychnine. J Org Chem 1993;58:7490-7497.
3. b) Rawal VH, Isawa S. Total synthesis of (±)-strychnine. J Org Chem 1994;59:2685-2686 and references therein.
4. Knight SD, Overman LE, Pairaudeau G. Total synthesis of (-)-strychnine. J Am Chem Soc 1995;117:5776-5788.
5. Solè D, Bonjoch J, Garcia-Rubio S, Peidû E, Bosch J. Total synthesis of (-)-strychnine. Angew Chem Int Ed Eng 1999;38:395-397 and references therein.
6. Shimizu S, Ohori K, Arai T, Sasai H, Shibasaki M. Our previous catalytic asymmetric synthesis of Strychnos alkaloids. J Org Chem 1998; 63:7547-7551.
7. a) Arai T, Yamada YMA, Yamamoto N, Sasai H, Shibasaki M. Our catalytic asymmetric Michael addition using the heterobimetallic catalysts. Chem Eur J 1996;2:1368-1378.
8. b) Arai T, Sasai H, Yamaguchi K, Shibasaki M. Catalytic asymmetric Michael addition of phosphonates. J Am Chem Soc 1998;120:441-442.
9. Kump WG, Patel MB, Rowson JM, Schmid H. Isolation of 19.20-dihydroakuammicine. Helv Chim Acta 1964;47:1497-1503.
10. a) Aghoramurthy K, Robinson R. Partial synthesis of 19,20-dihydroakuammicine.Tetrahdron 1957;1:172-173.
11. b) Levy J, Men Le J, Jacot MM. Partial synthesis of 1. Bull Soc Chim Fr 1960;979-981.
12. Weissmann C, Schmid H, Karrer P. Partial synthesis of 1. Helv Chim Acta 1961;44:1877-1880.
13. a) Amat M, Linares A, Bosch J. Total synthesis of (±)-1. Tetrahedron Lett 1989;30:2293-2296.
14. b) Amat M, Linares A, Bosch J. Total syntheses of strychnos alkaloids. J Org Chem 1990;55:6299-6312.
15. Kuene ME, Frasier DA, Spitzer TD. Total synthesis of 19,20-dihydro-20-epiakuammicine. J Org Chem 1991;56:2696-2700.
16. Bonjoch J. Solè D, Garcìa-Rubio S, Bosch J. Total syntheses of strychnos alkaloids utilizing 3a-(2-Nitrophenyl)-hexahydroindole-4-one. J Am Chem Soc 1997;119: 7230-7240 and references therein.
17. a) Amat M, Coll M, Bosch J, Espinosa E, Molins E. Previous total synthesis of (-)-1. Tetrahedron Asymmetry 1997;8:935-948.
18. b) Amat M, Coll MD, Bosch J. Total synthesis of (-)-1 using enzyme. Tetrahedron 1995;51:10759-10770.
19. Sasai H, Arai T, Satow Y, Houk KN, Shibasaki M. The enantiomeric excess of 4 was determined. J Am Chem Soc 1995;117:6194-6198. See also ref 3.
20. Berger L. Corraz AJ. Regioselective Fisher indole synthesis. U.S. Patent No. 4,009,181, 1977.
21. Heathcook CH. General stereochemistry for the aldol reaction. In: Trost BM, editor. Comprehensive organic synthesis, vol. 2. New York: Pergamon Press; 1991. p 181-238.
22. 4. J Org Chem 1990;55:2552-2554.
23. 4. Tetrahedron Lett 1994;35:2401-2404.
24. 2O gives tetrahydrocarbazole-3-one. J Org Chem 1977;42: 1213-1216.
25. b) Magnus P, Sear NL, Kim CS, Vicker N. Construction of the D ring of Strychnos alkaloids using DDQ oxidation. J Org Chem 1992;57:70-78.
26. a) Trost BM, Murayama E. Studies of cyclization using the thionium ion initiated by DMTSf. J Am Chem Soc 1981;103:6529-6530.
27. b) Trost BM, Murayama E. Phenanthrene nucleus construction via thionium ions. Tetrahedron Lett 1982;23:1047-1050.
28. Trost BM, Sato T. DMTSF initiated organometallic additions and macrocyclizations of thioketals. J Am Chem Soc 1985;107:719-721.
29. a) Lenz GR. Photochemistry of enamides. Synthesis 1978;489-518.
30. b) Campbell AL, Lenz GR. The ground state and excited state reactions of enamides. Synthesis 1987;421-452.