Enantioselective synthesis of indole alkaloids from chiral lactams

Synlett

Volumn , Issue 2, 2011, Pages 143-160

  Amat, Mercedes ^a   Pérez, Maria ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

alkaloids; indoles; lactams; stereoselective synthesis; total synthesis

Indexed keywords

1 DEOXYGULONOJIRIMYCIN; ANABASINE; ANKORINE; ASPIDOSPERMINE; BENZO[A]QUINOLIZIDINE DERIVATIVE; CERMIZINE C; CONIINE; CORYNANTHINE; DECARBOMETHOXYTETRAHYDROSECODINE; DIHYDROCORYNANTHEOL; DIHYDROPRONIDINE; EMETINE; ERVATAMINE; GEISSOSCHIZINE; GEPHYROTOXIN; IBOGAINE; INDOLE ALKALOID; LACTAM; MONOMORINE I; PHENYLGLYCINE; PIPERIDINE DERIVATIVE; PUMILIOTOXIN; QUEBRACHAMINE; QUINOLIZIDINE DERIVATIVE; SECOLOGANIN; SILICINE; SOLENOPSIN A; STRICTOSIDINE; TRYPTOPHANOL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; POLYMERIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 78651401179     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259297     Document Type: Article

References (148)

1. Strunz G M., Findlay J A., In The Alkaloids Vol. 26 Brossi A Academic London 1985 89-183
2. Takahata H, Momose T, In The Alkaloids Vol. 44 Cordell G A. Academic San Diego 1993 189-256
3. Ohmiya S, Saito K, Murakoshi I, In The Alkaloids Vol. 47 Cordell G A. Academic San Diego 1995 1-114
4. Schneider M J., In Alkaloids: Chemical and Biological Perspectives Vol. 10 Pelletier S W. Pergamon Oxford 1996 155-299
5. Andersen R J., Van Soest R W. M., Kong F, In Alkaloids: Chemical and Biological Perspectives Vol. 10 Pelletier S W. Pergamon Oxford 1996 301-355
6. Daly J W., Garraffo H M., Spande T F., In Alkaloids: Chemical and Biological Perspectives Vol. 13 Pelletier S W. Pergamon New York 1999 1-161
7. Watson P S., Jiang B, Scott B, Org. Lett. 2000 2 3679-3681
8. Michael J P., Nat. Prod. Rep. 2005 22 603-626
9. Angle S R., Breitenbucher J G., In Studies in Natural Products Chemistry Vol. 16 Atta-ur-Rahman Elsevier Amsterdam 1995 453-502
10. Laschat S, Dickner T, Synthesis 2000 1781
11. Guilloteau-Bertin B, Compère D, Gil L, Marazano C, Das B C., Eur. J. Org. Chem. 2000 1391
12. Weintraub P M., Sabol J S., Kane J M., Borcherding D R., Tetrahedron 2003 59 2953
13. Horton D A., Bourne G T., Smythe M L., Chem. Rev. 2003 103 893
14. Buffat M G. P., Tetrahedron 2004 60 1701
15. Pearson M S. M., Mathe-Allainmat M, Fargeas V, Lebreton J, Eur. J. Org. Chem. 2005 2159
16. Fraser H L., Floyd M B., Sosa A C. B., Prog. Heterocycl. Chem. 2005 17 261
17. Huang P.-Q, Synlett 2006 1133
18. De Risis C, Fanton G, Pollini G P., Trapella C, Valente F, Zanirato V, Tetrahedron: Asymmetry 2008 19 131
19. Kaellstroem S, Leino R, Bioorg. Med. Chem. 2008 16 601
20. Vicario J L., Badía D, Carrillo L, Ruiz N, Reyes E, In Targets in Heterocyclic Systems: Chemistry and Properties Vol. 12 Attanasi O A. Spinelli D Italian Society of Chemistry Rome 2008 302-327
21. Romo D, Meyers A I., Tetrahedron 1991 47 9503
22. Stereocontrolled Organic Synthesis Trost B M. Blackwell Oxford 1994
23. Meyers A I., Brengel G P., Chem. Commun. (Cambridge) 1997 1
24. Groaning M D., Meyers A I., Tetrahedron 2000 56 9843
25. Amat M, Llor N, Hidalgo J, Bosch J, Molins E, Miravitlles C, Tetrahedron: Asymmetry 1996 7 2501
26. Amat M, Llor N, Bosch J, Solans X, Tetrahedron 1997 53 719
27. Amat M, Bosch J, Hidalgo J, Cantó M, Pérez M, Llor N, Molins E, Miravitlles C, Orozco M, Luque J, J. Org. Chem. 2000 65 3074
28. Amat M, Llor N, Huguet M, Molins E, Espinosa E, Bosch J, Org. Lett. 2001 3 3257
29. Amat M, Cantó M, Llor N, Bosch J, Chem. Commun. (Cambridge) 2002 526
30. Amat M, Llor N, Escolano C, Huguet M, Pérez M, Molins E, Bosch J, Tetrahedron: Asymmetry 2003 14 293
31. Amat M, Llor N, Hidalgo J, Escolano C, Bosch J, J. Org. Chem. 2003 68 1919
32. Amat M, Escolano C, Llor N, Huguet M, Pérez M, Bosch J, Tetrahedron: Asymmetry 2003 14 1679
33. Casamitjana N, Amat M, Llor N, Carreras M, Pujol X, Fernández M M., López V, Molins E, Miravitlles C, Bosch J, Tetrahedron: Asymmetry 2003 14 2033
34. Amat M, Huguet M, Llor N, Bassas O, Gomez A M., Bosch J, Badia J, Baldoma L, Aguilar J, Tetrahedron Lett. 2004 45 5355
35. Amat M, Cantó M, Llor N, Ponzo V, Pérez M, Bosch J, Angew. Chem. Int. Ed. 2002 41 335
36. Amat M, Cantó M, Llor N, Escolano C, Molins E, Espinosa E, Bosch J, J. Org. Chem. 2002 67 5343
37. Amat M, Bassas O, Pericàs M A., Pastó M, Bosch J, Chem. Commun. (Cambridge) 2005 1327
38. Amat M, Bassas O, Llor N, Cantó M, Pérez M, Molins E, Bosch J, Chem. Eur. J. 2006 12 7872
39. Amat M, Pérez M, Llor N, Bosch J, Lago E, Molins E, Org. Lett. 2001 3 611
40. Amat M, Pérez M, Llor N, Bosch J, Org. Lett. 2002 4 2787
41. Amat M, Pérez M, Minaglia A T., Casamitjana N, Bosch J, Org. Lett. 2005 7 3653
42. Soteras I, Lozano O, Gómez-Esqué A, Escolano C, Orozco M, Amat M, Bosch J, Luque F J., J. Am. Chem. Soc. 2006 128 6581
43. Amat M, Escolano C, Gómez-Esqué A, Lozano O, Llor N, Griera R, Molins E, Bosch J, Tetrahedron: Asymmetry 2006 17 1581
44. Allin S M., Duffy L J., Bulman Page P C., McKee V, Edgar M, McKenzie M J., Amat M, Bassas O, Santos M M. M., Bosch J, Tetrahedron Lett. 2006 47 5713
45. Amat M, Pérez M, Minaglia A T., Peretto B, Bosch J, Tetrahedron 2007 63 5839
46. Amat M, Pérez M, Minaglia A T., Bosch J, J. Org. Chem. 2008 73 6920
47. Amat M, Pérez M, Minaglia A T., Passarella D, Bosch J, Tetrahedron: Asymmetry 2008 19 2406
48. Amat M, Brunaccini E, Checa B, Pérez M, Llor N, Bosch J, Org. Lett. 2009 11 4370
49. Amat M, Pérez M, Proto S, Gatti T, Bosch J, Chem. Eur. J. 2010 16 9438
50. Amat M, Griera R, Fabregat R, Molins E, Bosch J, Angew. Chem. Int. Ed. 2008 47 3348
51. Amat M, Fabregat R, Griera R, Bosch J, J. Org. Chem. 2009 74 1794
52. Amat M, Fabregat R, Griera R, Florindo P, Molins E, Bosch J, J. Org. Chem. 2010 75 3797
53. Escolano C, Amat M, Bosch J, Chem. Eur. J. 2006 12 8198
54. Gaskell S N., Duffy L J., Allin S M., Nat. Prod. Commun. 2008 3 1825
55. Indoles: The Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds Vol. 25, Part 4 Saxton J E. Weissberger A Taylor E C. Wiley New York 1983
56. Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds Suppl. to Vol. 25, Part 4 Saxton J E. Taylor E C. Wiley Chichester 1994
57. Leonard J, Nat. Prod. Rep. 1999 16 319
58. Borschberg H.-J, Curr. Org. Chem. 2005 9 1465
59. Edwankar C R., Edwankar R V., Namjoshi O A., Rallapalli S K., Yang J, Cook J M., Curr. Opin. Drug Discovery Dev. 2009 12 752
60. O'Connor S E., Maresh J J., Nat. Prod. Rep. 2006 23 532
61. Stöckigt J, Barleben L, Panjikar S, Loris E A., Plant Physiol. Biochem. 2008 46 340
62. Danieli B, Palmisano G, In The Alkaloids Vol. 27 Brossi A Academic Orlando 1986 1-130
63. Scott A I., Acc. Chem. Res. 1970 3 151
64. Amat M, Llor N, Hidalgo J, Bosch J, Tetrahedron: Asymmetry 1997 8 2237
65. Amat M, Escolano C, Llor N, Lozano O, Gómez-Esqué A, Griera R, Bosch J, ARKIVOC 2005 (ix) 115
66. Amat M, Pshenichnyi G, Bosch J, Molins E, Miravitlles C, Tetrahedron: Asymmetry 1996 7 3091 See also ref. 15
67. Crooks P A., Robinson B, Smith G F., Chem. Commun. 1968 1210
68. Robert G M. T., Ahond A, Poupat C, Potier P, Jollés C, Jousselin A, Jacquemin H, J. Nat. Prod. 1983 46 694
69. Atta-ur-Rahman, Zaman K, Perveen S, Habib-ur-Rehman, Muzaffar A, Choudhary M I., Pervin A, Phytochemistry 1991 30 1285
70. Mroue M A., Ghuman M A., Alam M, Phytochemistry 1993 33 217
71. Palmisano G, Santagostino M, Riva S, Sisti M, Tetrahedron: Asymmetry 1995 6 1229
72. Amat M, Hadida S, Sathyanarayana S, Bosch J, J. Org. Chem. 1994 59 10
73. Battersby A R., Parry R J., J. Chem. Soc. D 1971 901
74. Jain S, Sinha A, Bhakuni D S., Phytochemistry 2002 60 853
75. Uskokovic M, Reese C, Lee H L., Grethe G, Gutzwiller J, J. Am. Chem. Soc. 1971 93 5902
76. Uskokovic M R., Henderson T, Reese C, Lee H L., Grethe G, Gutzwiller J, J. Am. Chem. Soc. 1978 100 571
77. Fujii T, Ohba M, Yoneyama K, Kizu H, Chem. Pharm. Bull. 1985 33 358
78. Minato D, Imai M, Kanda Y, Onomura O, Matsumura Y, Tetrahedron Lett. 2006 47 5485
79. Fujii T, Yoshifuji S, Tai M, Chem. Pharm. Bull. 1975 23 2094
80. Fujii T, Ohba M, Chem. Pharm. Bull. 1985 33 583
81. Brown R T., Leonard J, Tetrahedron Lett. 1978 19 1605
82. Hirai Y, Terada T, Yamazaki T, Momose T, J. Chem. Soc., Perkin Trans. 1 1992 517
83. Hirai Y, Terada T, Yamazaki T, Momose T, J. Chem. Soc., Perkin Trans. 1 1992 509
84. Amat M, Pérez M, Llor N, Escolano C, Luque F J., Molins E, Bosch J, J. Org. Chem. 2004 69 8681
85. Deslongchamps P, In Stereoelectronic Effects in Organic Chemistry Pergamon Oxford 1983 221
86. Perlmutter P, In Conjugate Addition Reactions in Organic Synthesis Pergamon Oxford 1992 25
87. Fujii T, Ohba M, Yoneyama K, Kizu H, Yoshifuji S, Chem. Pharm. Bull. 1986 34 669
88. Fujii T, Ohba M, Heterocycles 1998 47 525; and references cited therein
89. Edwin S J., In The Alkaloids Vol. 50 Cordell G A. Academic San Diego 1998 343-376
90. Overman L E., Sworin M, In Alkaloids: Chemical and Biological Perspectives Vol. 3 Pelletier S W. John Wiley and Sons New York 1985 275-307
91. Cordell G A., In The Alkaloids Vol. 17 Manske R H. F. Rodrigo R G. A. Academic New York 1979 199-384
92. Sundberg R J., Smith S Q., In The Alkaloids Vol. 59 Cordell G A. Elsevier San Diego 2002 281-386
93. Takayama H, Sakai S.-I, In The Alkaloids Vol. 50 Cordell G A. Elsevier San Diego 1998 415-452
94. Amat M, Lozano O, Escolano C, Molins E, Bosch J, J. Org. Chem. 2007 72 4431
95. Ziegler F E., Kloek J A., Zoretic P A., J. Am. Chem. Soc. 1969 91 2342
96. Ziegler F E., Bennett G B., J. Am. Chem. Soc. 1973 95 7458
97. Takano S, Sato M, Hatakema S, Hirama M, Ogasawara K, Heterocycles 1976 5 221
98. Takano S, Yonaga M, Ogasawara K, J. Chem. Soc., Chem. Commun. 1981 1153
99. Node M, Nagasawa H, Fuji K, J. Org. Chem. 1990 55 517
100. Kozmin S A., Iwama T, Huang Y, Rawal V H., J. Am. Chem. Soc. 2002 124 4628
101. Sattely E S., Meek S J., Malcolmson S J., Schrock R R., Hoveyda A H., J. Am. Chem. Soc. 2009 131 943
102. Amat M, Escolano C, Lozano O, Gómez-Esqué A, Griera R, Molins E, Bosch J, J. Org. Chem. 2006 71 3804
103. For a preliminary account of this work, see:, Amat M, Escolano C, Lozano O, Llor N, Bosch J, Org. Lett. 2003 5 3139
104. Danieli B, Lesma G, Passarella D, Silvani A, Tetrahedron Lett. 2000 41 3489
105. Kanada R M., Ogasawara K, Tetrahedron Lett. 2001 42 7311
106. Joule J A., Indoles: The Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds Vol. 25, Part 4 Saxton J E. Weissberger A Taylor E C. Wiley New York 1983 Chap. 6
107. Alvarez M, Joule J A., Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds Suppl. to Vol. 25, Part 4 Saxton J E. Taylor E C. Wiley Chichester 1994 Chap. 6
108. Alvarez M, Joule J A., In The Alkaloids Vol. 57 Cordell G A. Academic New York 2001 Chap. 4
109. Amat M, Llor N, Checa B, Pérez M, Bosch J, Tetrahedron Lett. 2007 48 6722
110. For a preliminary account of this work, see:, Amat M, Pérez M, Llor N, Martinelli M, Molins E, Bosch J, Chem. Commun. (Cambridge) 2004 1602
111. Saito M, Kawamura M, Hiroya K, Ogasawara K, Chem. Commun. (Cambridge) 1997 765
112. Joule J A., Ohashi M, Gilbert B, Djerasi C, Tetrahedron 1965 21 1717
113. Gràcia J, Casamitjana N, Bonjoch J, Bosch J, J. Org. Chem. 1994 59 3939
114. Ishikura M, Takahashi N, Yamada K, Abe T, Heterocycles 2008 75 107
115. Wu A, Snieckus V, Tetrahedron Lett. 1975 16 2057
116. Amat M, Coll M.-D, Bosch J, Espinosa E, Molins E, Tetrahedron: Asymmetry 1997 8 935
117. Joule J A., Indoles: The Monoterpenoid Indole Alkaloids, In The Chemistry of Heterocyclic Compounds Vol. 25, Part 4 Saxton J E. Weissberger A Taylor E C. Wiley New York 1983 232
118. Zhang H, Yue J.-M, Helv. Chim. Acta 2005 88 2537
119. Amat M, Llor N, Checa B, Molins E, Bosch J, J. Org. Chem. 2010 75 178
120. For related synthetic studies on the ervatamine-silicine group, see
121. Husson H.-P, Bannai K, Freire R, Mompon B, Reis F A. M., Tetrahedron 1978 34 1363
122. Bennasar M.-L, Vidal B, Bosch J, J. Org. Chem. 1997 62 3597
123. Bennasar M.-L, Vidal B, Kumar R, Lázaro A, Bosch J, Eur. J. Org. Chem. 2000 3919
124. Langlois Y, Potier P, Tetrahedron 1975 31 423
125. Grierson D S., Bettiol J.-L, Buck I, Husson H.-P, Rubiralta M, Diez A, J. Org. Chem. 1992 57 6414
126. For a preliminary account of this work, see:, Amat M, Checa B, Llor N, Molins E, Bosch J, Chem. Commun. (Cambridge) 2009 2935
127. Bassas O, Llor N, Santos M M. M., Griera R, Molins E, Amat M, Bosch J, Org. Lett. 2005 7 2817
128. Amat M, Santos M M. M., Bassas O, Llor N, Escolano C, Gómez-Esqué A, Molins E, Allin S M., McKee V, Bosch J, J. Org. Chem. 2007 72 5193
129. Santos M M. M., In Heterocyclic Targets in Advanced Organic Synthesis Carreiras M C. Marco-Contelles J Research Signpost Trivandrum / India 2001 69-82
130. Allin S M., Thomas C I., Allard J E., Duncton M, Elsegood M R. J., Edgar M, Tetrahedron Lett. 2003 44 2335
131. Allin S M., Thomas C I., Allard J E., Doyle K, Elsegood M R. J., Tetrahedron Lett. 2004 45 7103
132. Allin S M., Thomas C I., Allard J E., Doyle K, Elsegood M R. J., Eur. J. Org. Chem. 2005 4179
133. Allin S M., Northfield C J., Page M I., Slawin A M. Z., Tetrahedron Lett. 1998 39 4905
134. Allin S M., Gaskell S N., Elsegood M R. J., Martin W P., Tetrahedron Lett. 2007 48 5669
135. Allin S M., Thomas C I., Doyle K, Elsegood M R. J., J. Org. Chem. 2005 70 357
136. Amat M, G ómez-Esqué A, Escolano C, Santos M M. M., Molins E, Bosch J, J. Org. Chem. 2009 74 1205
137. Tietze L F., Zhou Y, Angew. Chem. Int. Ed. 1999 38 2045
138. Weisbach J A., Kirkpatrick J L., Williams K R., Anderson E L., Yim N C., Douglas B, Tetrahedron Lett. 1965 6 3457
139. Van Tamelen E E., Hester J.B. Jr., J. Am. Chem. Soc. 1969 91 7342
140. Brown R T., Jones M F., Wingfield M, J. Chem. Soc., Chem. Commun. 1984 847
141. Diez A, Vila C, Sinibaldi M E., Troin Y, Rubiralta M, Tetrahedron Lett. 1993 34 733
142. For previous syntheses of (-)-dihydrocorynantheol, see:, Suzuki T, Sato E, Unno K, Kametani T, Chem. Pharm. Bull. 1986 34 1584
143. Beard R L., Meyers A I., J. Org. Chem. 1991 56 2091
144. Ohba M, Ohashi T, Fujii T, Heterocycles 1991 32 319
145. Itoh T, Tokoya M, Miyauchi K, Nagata K, Ohsawa A, Org. Lett. 2006 8 1533
146. Tosaka A, Ito S, Miyazawa N, Shibuya M, Ogasawara K, Iwabuchi Y, Heterocycles 2006 70 153
147. Deiters A, Pettersson M, Martin S F., J. Org. Chem. 2006 71 6547
148. For the conversion of (-)-dihydrocorynantheine into (-)-rhynchophylline and (+)-isorhynchophylline, see:, Finch N, Taylor W I., J. Am. Chem. Soc. 1962 84 3871