Enantioselective synthesis of alkaloids from phenylglycinol-derived lactams

Natural Product Communications

Volumn 6, Issue 4, 2011, Pages 515-526

  Amat, Mercedes ^a   Llor, Núria ^a   Griera, Rosa ^a   Pérez, Maria ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Alkaloids; Indole; Lactams; Phenylglycinol; Piperidine; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; ANABASINE; ASPIDOSPERMIDINE; CERMIZINE C; CONIINE; DECARBOMETHOXYTETRAHYDROSECODINE; DEOXY DEXTRO GULONOJIRIMYCIN; DIHYDROCLEAVAMINE; DIHYDROPINIDINE; EPIULEINE; FEMOXETINE; GEPHYROTOXIN 167B; LACTAM DERIVATIVE; LUPETIDINE; MADANGAMINE A; MADANGAMINE B; MADANGAMINE C; MADANGAMINE D; MADANGAMINE E; MADANGAMINE F; MONOMORINE; PAROXETINE; PHENYLGLYCINOL DERIVED OXAZOLOPIPERIDONE LACTAM DERIVATIVE; PRECLAMOL; PUMILIOTOXIN C; QUEBRACHEMINE; SOLENOPSIN A; ULEINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBURNINE;

ADDITION REACTION; ALKYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REVIEW;

EID: 79955834587     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1100600412     Document Type: Review

References (66)

1. For alternative procedures, see: (a) Royer J, Husson HP. (1993) A new potential acyl iminium ion for the asymmetric synthesis of piperidine derivatives. Heterocycles, 1493-1496;
2. (b) Terán JL, Gnecco D, Galindo A, Juárez J, Bernès S, Enríquez RG. (2001) New methodology for the synthesis of enantiopure (3R,2aR)-(-)-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-one: a synthesis of (S)-(+)-coniine. Tetrahedron: Asymmetry, 12, 357-360;
3. (c) Airiau E, Spangenberg T, Girard N, Schoenfelder A, Salvadori J, Taddei M, Mann A. (2008) A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation. Chemistry, A European Journal, 14, 10938-10948;
4. (d) Tojino M, Otsuka N, Fukuyama T, Matsubara H, Ryu I. (2006) Selective 6-endo cyclization of the acyl radicals onto the nitrogen of imine and oxazoline C-N bonds Journal of American Chemistry Society, 128, 7712-7713. (Pubitemid 43945694)
5. Romo D, Meyers AI. (1991) Chiral non-racemic bicyclic lactams. Vehicles for the construction of natural and unnatural products containing quaternary carbon centers. Tetrahedron, 47, 9503-9569.
6. (a) Meyers AI, Brengel GP. (1997) Chiral bicyclic lactams: useful precursors and templates for asymmetric syntheses. Chemical Communications, 1-8;
7. (b) Groaning MD, Meyers AI. (2000) Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions. Tetrahedron, 56, 9843-9873.
8. Escolano C, Amat M, Bosch J. (2006) Chiral oxazolopiperidone lactams: versatile intermediates for the enantioselective synthesis of piperidine-containing natural products. Chemistry, A European Journal, 12, 8198-8207. (Pubitemid 44759817)
9. (a) Kong F, Andersen RJ, Allen TM. (1994) Madangamine A, a novel cytotoxic alkaloid from the marine sponge Xestospongia ingens. Journal of the American Chemical Society, 116, 6007-6008;
10. (b) Kong F, Graziani EI, Andersen RJ. (1998) Madangamines B-E, pentacyclic alkaloids from the marine sponge Xestospongia ingens. Journal of Natural Products, 61, 267-271;
11. (c) De Oliveira JHHL, Nascimento AM, Kossuga MH, Cavalcanti BC, Pessoa CO, Moraes MO, Macedo ML, Ferreira AG, Hajdu E, Pinheiro US, Berlinck RGS. (2007) Cytotoxic alkylpiperidine alkaloids from the brazilian marine sponge Pachychalina alcaloidifera. Journal of Natural Products, 70, 538-543. (Pubitemid 46797852)
12. (a) Amat M, Pérez M, Minaglia AT, Casamitjana N, Bosch J. (2005) An enantioselective entry to cis-perhydroisoquinolines. Organic Letters, 7, 3653-3656;
13. (b) Amat M, Pérez M, Proto S, Gatti T, Bosch J. (2010) First enantioselective synthesis of the diazatricyclic core of madangamine alkaloids. Chemistry, A European Journal, 16, 9438-9441.
14. Matzanke N, Gregg RJ, Weinreb SM. (1997) A concise approach to the tricyclic core of the cytotoxic marine alkaloid Madangamine A. The Journal of Organic Chemistry, 62, 1920-1921. (Pubitemid 27213875)
15. rd EuCheMS Chemistry Congress, Nürnberg, Germany.
16. Daly JW, Spande TF, Garraffo HM. (2005) Alkaloids from amphibian skin: A tabulation of over eight-hundred compounds. Journal of Natural Products, 68, 1556-1575. (Pubitemid 41658912)
17. Daly JW, Tokuyama T, Habermehl G, Karle IL, Witkop B. (1969) Isolierung und struktur von pumiliotoxin C. Justus Liebigs Annalen der Chemie, 729, 198-204.
18. (a) Witkop B, Gössinger E. (1983) Amphibian alkaloids. In The Alkaloids. Vol. 21, Brossi, A. (Ed). Academic Press, New York, 139-253;
19. (b) Daly JW, Spande TF. (1986) Amphibian alkaloids: Chemistry, pharmacology, and biology. In Alkaloids: Chemical and Biological Perspectives. Vol. 4, Pelletier SW. (Ed). Wiley, New York, 1-274;
20. (c) Winterfeldt E. (1979) Recent progress in alkaloid synthesis. Heterocycles, 12, 1631-1650;
21. (d) Scholz U, Winterfeldt E. (2000) Biomimetic synthesis of alkaloids. Natural Products Report, 17, 349-366. (Pubitemid 30620864)
22. (a) Amat M, Griera R, Fabregat R, Molins E, Bosch J. (2008) A biomimetic enantioselective approach to the decahydroquinoline class of dendrobatid alkaloids. Angewandte Chemie International Edition, 47, 3348-3351;
23. (b) Amat M, Fabregat R, Griera R, Florindo P, Molins E, Bosch J. (2010) Biomimetic construction of the hydroquinoline ring system. Diastereodivergent enantioselective synthesis of 2,5-disubstituted cis-decahydroquinolines. The Journal of Organic Chemistry, 75, 3797-3805.
24. Amat M, Fabregat R, Griera R, Bosch J. (2009) A general synthetic route to enantiopure 5-substituted cis-decahydroquinolines. The Journal of Organic Chemistry, 74, 1794-1797.
25. (a) Cordell, GA. (1983) The ibogamine-catharanthine group. In Indoles. The Monoterpenoid Indole Alkaloids. Vol. 25, Saxton JE. (Ed). In The Chemistry of Heterocyclic Compounds; Weissberger A, Taylor EC. (Eds). Wiley, New York, part 4, 467-537;
26. (b) Saxon JE. (1994) The ibogamine-catharanthine group. In Indoles. The Monoterpenoid Indole Alkaloids. Vol. 25, Saxton JE. (Ed). In The Chemistry of Heterocyclic Compounds; Weissberger A, Taylor EC. (Eds). Wiley, Chichester, Suppl. to part 4, 487-521.
27. (a) Saxon JE. (1983) The aspidospermine group. In Indoles. The Monoterpenoid Indole Alkaloids. Vol. 25, Saxton JE. (Ed). In The Chemistry of Heterocyclic Compounds; Weissberger A, Taylor EC. (Eds). Wiley, New York, part 4, 331-465;
28. (b) Saxon JE. (1994) The aspidospermine group. In Indoles. The Monoterpenoid Indole Alkaloids. Vol. 25, Saxton JE. (Ed). In The Chemistry of Heterocyclic Compounds; Weissberger A, Taylor EC. (Eds). Wiley, Chichester, Suppl. to part 4, 357-436.
29. (a) Amat M, Escolano C, Lozano O, Llor N, Bosch J. (2003) Enantioselective synthesis of cis- and trans-3,5-disubstituted piperidines. Synthesis of 20S- and 20R-dihydrocleavamine. Organic Letters, 5, 3139-3142;
30. (b) Amat M, Escolano C, Lozano O, Gómez-Esqué A, Griera R, Molins E, Bosch J. (2006) Alkylation of phenylglycinol-derived oxazolopiperidone lactams. Enantioselective synthesis of β-substituted piperidines. The Journal of Organic Chemistry, 71, 3804-2815.
31. Amat M, Escolano C, Gómez-Esqué A, Lozano O, Llor N, Griera R, Molins E, Bosch J. (2006) Stereoselective α-amidoalkylation of phenylglycinol-derived lactams. Synthesis of enantiopure 5,6-disubstituted 2-piperidones. Tetrahedron: Asymmetry, 17, 1581-1588. (Pubitemid 43947595)
32. Danieli B, Lesma G, Passarella D, Silvani A. (2000) Indole alkaloids by a chemoenzymatic approach: two convergent routes for the first enantioselective synthesis of (+)-20R-15,20-dihydrocleavamine. Tetrahedron Letters, 41, 3489-3492. (Pubitemid 30307843)
33. Amat M, Lozano O, Escolano C, Molins E, Bosch J. (2007) Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams. The Journal of Organic Chemistry, 72, 4431-4439. (Pubitemid 46903314)
34. (a) Ziegler FE, Kloek JA, Zoretic PA. (1969) Synthesis of quebrachamine and 3,4-dehydroquebrachamine. Journal of the American Chemical Society, 91, 2342-2346;
35. (b) Irie K, Ban Y. (1981) Total synthesis of (±)-eburnamonine and (±)-epieburnamonine Heterocycles, 15, 201-206;
36. (c) Imanishi T, Miyashita. K, Nakai A, Inoue M, Hanaoka M. (1983) 1,6-Dihydro-3(2H)-pyridinones. V. Total synthesis of (±)-eburnamonine Chemical & Pharmaceutical Bulletin, 31, 1191-1198;
37. (d) Wenkert E, Hudlicky T. (1988) Synthesis of eburnamonine and dehydroaspidospermidine. The Journal of Organic Chemistry, 53, 1953-1957.
38. (a) Joule JA. (1983) The uleine-ellipticine-vallesamine group. In Indoles. The Monoterpenoid Indole Alkaloids. Vol. 25, Saxton JE. (Ed). In The Chemistry of Heterocyclic Compounds, Weissberger A, Taylor EC. (Eds). Wiley, New York, Part 4, Chapter 6;
39. (b) Alvarez M, Joule JA. (1994) The akuammidine-quebrachidine-ervatamine- gelsemine-akuammiline group. In Monoterpenoid Indole Alkaloids. Vol. 25, Saxton JE. (Ed). In The Chemistry of Heterocyclic Compounds; Taylor EC. (Ed). Wiley, Chichester, Suppl. to Part 4, Chapter 6;
40. (c) Alvarez M, Joule JA. (2001) Ellipticine, uleine, apparicine and related alkaloids. In The Alkaloids. Vol. 57, Cordell GA. (Ed). Academic Press, New York, Chapter 4.
41. Le Men J, Taylor WI. (1965) A uniform numbering system for indole alkaloids. Experientia, 21, 508-510.
42. Amat M, Llor N, Checa B, Pérez M, Bosch J. (2007) Enantioselective synthesis of 2-[(3-ethyl-4-piperidyl)methyl]indoles from a phenylglycinol- derived lactam: formal synthesis of Strychnos alkaloids. Tetrahedron Letters, 48, 6722-6725. (Pubitemid 47284236)
43. (a) Wu A, Snieckus V. (1975) A new synthesis of a stemmadenine model. Tetrahedron Letters, 16, 2057-2060;
44. (b) Gràcia J, Casamitjana N, Bonjoch J, Bosch J. (1994) Total synthesis of uleine-type and Strychnos alkaloids through a common intermediate. The Journal of Organic Chemistry, 59, 3939-3951. (Pubitemid 24248151)
45. (a) Amat M, Pérez M, Llor N, Martinelli M, Molins E, Bosch J. (2004) Enantioselective formal synthesis of uleine alkaloids from phenylglycinol-derived bicyclic lactams. Chemical Communications, 1602-1603;
46. (b) Amat M, Pérez M, Llor N, Escolano C, Luque FJ, Molins E, Bosch J. (2004) Conjugate additions to phenylglycinol-derived unsaturated δ-lactams. Enantioselective synthesis of uleine alkaloids. The Journal of Organic Chemistry, 69, 8681-8693. (Pubitemid 39603027)
47. Saito M, Kawamura M, Hiroya K, Ogasawara K. (1997) First enantiocontrolled syntheses of (+)-uleine and (+)-dasycarpidone. Chemical Communications, 765-766. (Pubitemid 27193011)
48. Joule JA, Ohashi M, Gilbert B, Djerasi C. (1965) Alkaloid studies-LIII: The structures of nine new alkaloids from Aspidosperma dasycarpon A. DC. Tetrahedron, 21, 1717-1734.
49. (a) Joule JA. (1983) The ervatamine and ervitsine group. Alkaloids with (1) 5,16 and 6,16 bonds but no 5,6 bond and (2) 5,16 5,7, and 6,16 bonds but no 5,6 bond. In Indoles. The Monoterpenoid Indole Alkaloids. Vol. 25, Saxton JE. (Ed). In The chemistry of heterocyclic compounds; Weissberger A, Taylor EC. (Eds). Wiley, New York, part 4, 232-239,
50. (b) Danieli B, Palmisano G. (1986) Alkaloids from Tabernaemontana. In The Alkaloids, Vol. 27, Brossi A. (Ed). Academic Press, Orlando, 1-130.
51. (a) Zeches M, Debray MM, Ledouble G, Le Men-Olivier L, Le Men J. (1975) Alcaloïdes du Pandaca caducifolia. Phytochemistry, 14, 1122-1124,
52. (b) Clivio P, Richard B, Nuzillard JM, Zèches-Hanrot M. (1995) 16-epi-Silicine, an alkaloid of the ervatamine-type from Pandaca caducifolia. Phytochemistry, 40, 987-990.
53. (a) Amat M, Checa B, Llor N, Molins E, Bosch J. (2009) Enantioselective total synthesis of the indole alkaloid 16-episilicine. Chemical Communications, 2935-2937;
54. (b) Amat M, Checa B, Llor N, Molins E, Bosch J. (2010) A synthetic approach to ervatamine-silicine alkaloids. Enantioselective total synthesis of (-)-16-episilicine. The Journal of Organic Chemistry, 75, 178-189.
55. (a) Phillipson JD, Roberts MF, Zenk MH. (Ed). (1985) The Chemistry and Biology of Isoquinoline Alkaloids, Springer-Verlag, Berlín;
56. (b) Atta-ur-Rahman (1994) In Handbook of Natural Products Data, Vol. 3, Elsevier, Amsterdam;
57. (c) Scott JD, Williams RM. (2002) Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. Chemical Reviews, 102, 1669-1730;
58. (d) Dewick PM. (2002) Alkaloids derived from tyrosine phenylethylamines and simple tetrahydroisoquinoline alkaloids. In Medicinal Natural Products, Wiley, Chichester, 315-346;
59. (e) Bentley KW. (2006) β-Phenylethylamines and the isoquinoline alkaloids. Natural Products Report, 23, 444-463.
60. (a) Munchhof MJ, Meyers AI. (1995) A novel route to chiral, nonracemic 1-alkyl- and 1-aryl-substituted tetrahydroisoquinolines. Synthesis of (-)-salsolidine and (+)-cryptostyline II. The Journal of Organic Chemistry, 60, 7086-7087;
61. (b) Munchhof MJ, Meyers AI. (1996) A novel asymmetric route to the 1,3-disubstituted tetrahydroisoquinoline, (-)-argemonine. The Journal of Organic Chemistry, 61, 4607-4610. (Pubitemid 26247673)
62. Amat M, Elias V, Llor N, Subrizi F, Molins E, Bosch J. (2010) A general methodology for the enantioselective synthesis of 1-substituted tetrahydroisoquinoline alkaloids. European Journal of Organic Chemistry, 4017-4026.
63. (a) Battersby AR, Edwads TP. (1960) Chemical correlation of the absolute configurations of salsolidine, salsoline, and calycotomine with the amino-acids. Journal of the Chemical Society, 1214-1221;
64. (b) Brossi A, Teitel S. (1971) Synthesis and absolute configuration of cryptostylines I, II, and III. Helvetica Chimica Acta, 54, 1564-1571;
65. (c) Leboeuf M, Cavé A, Touché A, Provost J, Forgacs P. (1981) Isolement de l'Higénaminea a partir de l'Annona squamosa; interet des résines adsorbantes macromoléculaires en chime végétale extractive. Journal of Natural Products, 44, 53-60;
66. (d) Yamazaki N, Suzuki H, Aoyagi S, Kibayashi C. (1996) Lewis acid-mediated nucleophilic alkylations on chiral [6,3a,4]oxadiazaindano[5,4-a] isoquinolines. Asymmetric synthesis of 1-alkyl substituted tetrahydroisoquinolines. Tetrahedron Letters, 37, 6161-6164. (Pubitemid 26259541)