Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis

Accounts of Chemical Research

Volumn 35, Issue 10, 2002, Pages 895-904

  Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBONYL DERIVATIVE; DELTA AMINOCARBONYL DERIVATIVE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; NATURAL PRODUCT; NITROGEN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; ENANTIOSELECTIVITY; MANNICH REACTION; MOLECULAR DYNAMICS; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

ALKALOIDS; CHEMISTRY, ORGANIC; FURANS; MOLECULAR STRUCTURE;

EID: 0036796894     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar950230w     Document Type: Article

References (44)

1. Arend, M.; Westermann, B.; Risch, N. Modern Variants of the Mannich Reaction. Angew. Chemie, Int. Ed. 1998, 37, 1044-1070.
2. Bur, S. K.; Martin, S. F. Vinylogous Mannich Reactions: Selectivity and Synthetic Utility. Tetrahedron 2001, 57, 3221-3242.
3. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. The Vinylogous Aldol Reaction: A Valuable, Yet Understated CarbonCarbon Bond-Forming Maneuver. Chem. Rev. 2000, 100, 1929-1972.
4. Martin, S. F.; Benage, B.; Williamson, S. A.; Brown, S. P. Applications of the Intramolecular Diels-Alder Reaction of Heterodienes to the Syntheses of Indole Alkaloids. Tetrahedron 1986, 42, 2903-2910.
5. Gutzwiller, J.; Pizzolato, G.; Uskokovic, M. A Novel Synthesis of Racemic Ajmalicine, 19-Epiajmalicine, Tetrahydroalstonine, and Akuammigine. J. Am. Chem. Soc. 1971, 93, 5907-5908.
6. Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. General Strategies for the Synthesis of Indole Alkaloids. Total Synthesis of (±)-Reserpine and (±)-α-Yohimbine. J. Am. Chem. Soc. 1987, 109, 6124-6134.
7. Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. Unified Strategy for the Synthesis of Indole and 2-Oxindole Alkaloids. J. Am. Chem. Soc. 1991, 113, 6161-6171.
8. Brands, K. M. J.; Pandit, U. K. Synthesis of the 'Tricyclic Heart' of Manzamines. Tetrahedron Lett. 1989, 30, 1423-1426.
9. Mooiweer, H. H.; Ettema, K. W. A.; Hiemstra, H.; Speckamp, W. N. Preparation of γ-Oxo-α-amino Acids from Silyl Enol Ethers and Glycine Cation Equivalent; a Facile Synthesis of (±)-5-Hydroxy-4-oxonorvaline (HON). Tetrahedron 1990, 46, 2991-2998.
10. Martin, S. F.; Benage, B.; Hunter, J. E. A Concise Strategy for the Total Syntheses of the Indole Alkaloids (±)-Tetrahydroalstonine, (±)-Geissoschizine and (±)-Cathenamine. J. Am. Chem. Soc. 1988, 110, 5925-5927.
11. Martin, S. F.; Mortimore, M. New Methods for the Synthesis of Oxindole Alkaloids. Total Syntheses of Isopteropodine and Pteropodine. Tetrahedron Lett. 1990, 31, 4557-4560.
12. Martin, S. F.; Geraci, L. S. A Concise Approach to the Aromatic Yohimboid and Protoberberine Alkaloids via Intramolecular Diels-Alder Reactions. Tetrahedron Lett. 1988, 29, 6725-6728.
13. Battersby, A. R.; Hall, E. S. The Intermediacy of Geissoschizine in Indole Alkaloid Biosynthesis: Rearrangement to the Strychnos Skeleton. J. Chem. Soc., Chem. Commun. 1969, 793-794.
14. Scott, A. I.; Cherry, P. C.; Qureshi, A. A. Mechanisms of Indole Alkaloid Biosynthesis: The Corynanthe-Strychnos Relationship. J. Am. Chem. Soc. 1969, 91, 4932-4933.
15. Heimberger, S. I.; Scott, A. I. Biosynthesis of Strychnine. J. Chem. Soc., Chem. Commun. 1973, 217-218.
16. Martin, S. F.; Clark, C. C.; Ito, M.; Mortimore, M. A Biomimetic Approach to the Strychnos Alkaloids. A Novel, Concise Synthesis of (±)-Akuammicine and a Route to (±)-Strychnine. J. Am. Chem. Soc. 1996, 118, 9804-9805.
17. Ito, M.; Clark, C. C.; Mortimore, M.; Goh, J. B.; Martin, S. F. Biogenetically Inspired Approach to the Strychnos Alkaloids. Concise Syntheses of (±)-Akuammicine and (±)-Strychnine. J. Am. Chem. Soc. 2001, 123, 8003-8010.
18. Knight, S. D.; Overman, L. E.; Pairaudeau, G. Asymmetric Total Syntheses of (-)- and (+)-Strychnine and the Wieland-Gumlich Aldehyde. J. Am. Chem. Soc. 1995, 117, 5776-5788.
19. Martin, S. F.; Clark, C. C.; Corbett, J. W. Applications of Vinylogous Mannich Reactions. Asymmetric Synthesis of the Heteroyohimboid Alkaloids (-)-Ajmalicine, (+)-19-epi-Ajmalicine, and (-)-Tetrahydroalstonine. J. Org. Chem. 1995, 60, 3236-3242.
20. Barton, D. H. R.; Crich, D.; Motherwell, W. B. The Invention of New Radical Chain Reactions. Part VIII. Radical Chemistry of Thiohydroxamic Esters: A New Method for the Generation of Carbon Radicals from Carboxylic Acids. Tetrahedron 1985, 41, 3901-3924.
21. van Tamelen, E. E.; Placeway, C.; Schiemenz, G. P.; Wright, I. G. Total Syntheses of dl-Ajmalicine and Emetine. J. Am. Chem. Soc. 1969, 91, 7359-7371.
22. Martin, S. F.; Chen, K. X.; Eary, C. T. An Enantioselective Total Synthesis of (+)-Geissoschizine. Org. Lett. 1999, 1, 79-81.
23. Martin, S. F.; Corbett, J. W. The Stereochemical Course of Nucleophilic Additions of 2-Trialkylsiloxyfurans to Cyclic N-Acyliminium Ions. Synthesis 1992, 55-57.
24. Morimoto, Y.; Nishida, K.; Hayashi, Y. An Efficient Approach toward Pyrrolidinyllactone System Characteristic of the Stemona Alkaloids. Lewis Acid-Catalyzed Stereoselective Reaction of N-Benzyloxycarbonyl-2-methoxypyrrolidine with 3-methyl-2-trimethylsiloxyfuran. Tetrahedron Lett. 1993, 34, 5773-5776.
25. Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. Applications of Vinylogous Mannich Reactions. Concise Asymmetric Total Syntheses of (+)-Croomine. J. Am. Chem. Soc. 1999, 121, 6990-6997.
26. Bur, S. K.; Martin, S. F. Vinylogous Mannich Reactions: Some Theoretical Studies on the Origins of Diastereoselectivity. Org. Lett. 2000, 2, 3445-3447.
27. Larsen, C. H.; Ridgeway, B. H.; Shaw, J. T.; Woerpel, K. A. A Stereoelectronic Model to Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions. J. Am. Chem. Soc. 1999, 121, 12208-12209.
28. Martin, S. F.; Lopez, O. D. Vinylogous Mannich Reactions. Catalytic, Asymmetric Additions of Triisopropylsilyloxyfurans to Aldimines. Tetrahedron Lett. 1999, 40, 8949-8953.
29. Martin, S. F.; Bur, S. K. The Stereochemical Course of Intramolecular Vinylogous Mannich Reactions. Tetrahedron Lett. 1997, 38, 7641-7644.
30. Rebek, J.; Shue, Y.-K.; Tai, D. F. The Rugulovasines: Synthesis, Structure, and Interconversions. J. Org. Chem. 1984, 49, 3540-3545.
31. Martin, S. F.; Liras, S. Novel Applications of Vinylogous Mannich Reactions. Total Synthesis of Rugulovasines A and B. J. Am. Chem. Soc. 1993, 115, 10450-10451.
32. Liras, S.; Lynch, C. L.; Fryer, A. M.; Vu, B. T.; Martin, S. F. Applications of Vinylogous Mannich Reactions. Total Syntheses of the Ergot Alkaloids Rugulovasines A and B and Setoclavine. J. Am. Chem. Soc. 2001, 123, 5918-5924.
33. Rebek, J. J.; Tai, D. F.; Shue, Y.-K. Synthesis of Ergot Alkaloids from Tryptophan. J. Am. Chem. Soc. 1984, 106, 1813-1819.
34. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. Enantioselective Synthesis of Pumiliotoxin 251D. A Strategy Employing an Allene-Based Electrophile-Mediated Cyclization. J. Am. Chem. Soc. 1991, 113, 2652-2656.
35. Martin, S. F.; Bur, S. K. Vinylogous Mannich Reactions. Stereo-selective Formal Synthesis of Pumiliotoxin 251D. Tetrahedron 1999, 55, 8905-8914.
36. Krafft, M. E.; Crooks, W. J. I.; Zorc, B.; Milczanowski, S. E. Reaction of Raney Nickel with Alcohols. J. Org. Chem. 1988, 53, 3158-3163.
37. Reichelt, A.; Bur, S. K.; Martin, S. F. Applications of Vinylogous Mannich Reactions. Enantioselective Synthesis of the Angiotensin Converting Enzyme Inhibitor (-)-A58365A. Tetrahedron, in press.
38. Fang, F. G.; Danishefsky, S. J. Total Synthesis of the Angiotensin-Converting Enzyme Inhibitor A58365A: On the Use of Pyroglutamate as a Chiral Educt. Tetrahedron Lett. 1989, 30, 3621-3624.
39. Martin, S. F.; Barr, K. J. Vinylogous Mannich Reactions. The Asymmetric Total Synthesis of (+)-Croomine. J. Am. Chem. Soc. 1996, 118, 3299-3300.
40. Dean, R. T.; Padgett, H. C.; Rapoport, H. A High Yield Regiospecific Preparation of Iminium Ion Salts. J. Am. Chem. Soc. 1976, 98, 7448-7449.
41. Csendes, I. G.; Lee, Y. Y.; Padgett, H. C.; Rapoport, H. Iminium Salts from α-Amino Acid Decarboxylation. Application to the Synthesis of Some 1-Azabicyclo[x.y.0] Systems. J. Org. Chem. 1979, 44, 4173-4178.
42. Hanessian, S.; McNaughton-Smith, G. A Versatile Synthesis of a β-Turn Peptidomimetic Scaffold: An Approach Towards a Designed Model Antagonist of the Tachykinin NK-2 Receptor. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572.
43. Casiraghi, G.; Rassu, G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers: Amsterdam, 1992; Vol. 11, pp 429-480.
44. Kende, A. S.; Hernando, J. I.; Milbank, J. B. J. First Total Synthesis of (±)-Stemonamide and (±)-Isostemonamide. Org. Lett. 2001, 3, 2505-2508.