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Synthesis 2001(16): 2365-2378
DOI: 10.1055/s-2001-18703
DOI: 10.1055/s-2001-18703
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Isolation, Total Synthesis and Biological Activity of Phenanthroindolizidine and Phenanthroquinolizidine Alkaloids
Weitere Informationen
Received
13 August 2001
Publikationsdatum:
05. August 2004 (online)
Publikationsverlauf
Publikationsdatum:
05. August 2004 (online)
Abstract
A review showing the efforts toward the isolation, total synthesis and biological activity of phenanthroindolizidine and phenanthroquinolizidine alkaloids from 1981 to 2000 is presented.
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1 Introduction
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2 Isolation of the Alkaloids
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3 Total Synthesis
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3.1 Directed Metallation of Tertiary Phenanthrene Amides
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3.2 Intramolecular Double Michael Reaction
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3.3 Biomimetic Synthesis
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3.4 Highly Enantioselective Amidoalkylations with N-Acylhydrazonium Salts
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3.5 Intramolecular Imino (Immonium) Diels-Alder Reaction
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3.6 Friedel-Crafts Acylation with N-(Trifluoroacetyl)-α-amino Acid Chloride
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3.7 Synthesis of (S)-(+)-Tylophorine or (S)-(+)-Cryptopleurine with (S)-(+)-Glutamic Acid or (S)-(+)-α-Aminoadipic Acid
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3.8 Intramolecular Cycloadditon of Azide with ω-Chloroalkene
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3.9 Thermal Ring Expansion of 4-(1-Pyrrolo)cyclobutenones
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3.10 Through Sterically Congested Pyridines
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3.11 Synthesis of (-)-Septicine and (-)-Tylophorine via Enantiopure N-Acyldihydropyridones
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3.12 Isomünchnone-based Method as Key Step
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3.13 Phosphorylated Cyclic Carbamate as Staring Material
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4 Biological Activity
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5 Conclusions
Key words
phenanthroindolizidine alkaloids - total synthesis - natural products - Diels-Alder reactions - intromolecular Michael additions - tylophorine - cryptopleurine
- 1
Ratnagiriswaran AN.Venkatachalam K. Indian J. Med. Res. 1935, 22: 433 - 2
Bick IRC.Sinchai W. The Alkaloids 1981, XIX: 193 - 3
Gellert E. J. Nat. Prod. 1982, 45: 50 - 4
Saifah E.Kelley CJ.Leary JD. J. Nat. Prod. 1983, 46: 353 - 5
Pettit GR.Goswami A.Cragg GM.Schmidt JM.Zou JC. J. Nat. Prod. 1984, 47: 913 - 6
Bhutani KK.Ali M.Atal CK. Phytochemistry 1984, 23: 1765 - 7
Ali M.Bhutani KK. Phytochemistry 1987, 26: 2089 - 8
Bhutani KK.Ali M.Atal CK. Phytochemistry 1985, 24: 2778 - 9
Ali M.Bhutani KK. Fitoterapia 1992, 63: 243; Chem. Abstr. 1992, 118: 219583f - 10
Fang SD.Zhang R.Chen Y.Xu CF. Acta Bot. Sin. 1989, 31: 934 - 11
Zhang R.Fang SD.Chen Y. Acta Bot. Sin. 1991, 33: 870 - 12
Ali M.Bhutani KK. Phytochemistry 1989, 28: 3513 - 13
Ali M.Ansari SH.Qadry JS. J. Nat. Prod. 1991, 54: 1271 - 14
Lavault M.Richomme P.Bruneton J. Pharm. Acta Helv. 1994, 68: 225 - 15
Abe F.Hirokawa M.Yamauchi T.Honda K.Hayashi N.Ishii M.Imagawa S.Iwahana M. Chem. Pharm. Bull. 1998, 46: 767 - 16
Wang QG.Xie L.Zhai JJ. Acta Cryst. 2000, C56: 197 - 17
Mirta SN.Rajan SS.Govindachari TR.Subramanian E. J. Chem. Crystallogr. 1996, 26: 223 - 18
Bradsher CK.Berger H. J. Am. Chem. Soc. 1958, 80: 930 - 19
Govindachari TR.Lakshmikantham MV.Rajaddura S. Tetrahedron 1961, 14: 284 - 20
Iwao M.Watanabe M.De Silva SO.Snieckus V. Tetrahedron Lett. 1981, 22: 2349 - 21
Iwao M.Mahalanabis KK.Watanabe M.Silva SO.Snieckus V. Tetrahedro 1983, 39: 1955 - 22
Ihara M.Tsuruta M.Fukumoto K.Kametani T. J. Chem. Soc., Chem. Commun. 1985, 1159 - 23
Govindachari TR.Pai BR.Nagarajan K. J. Chem. Soc. 1954, 2801 - 24
Govindachari TR.Rajapopalan TG.Viswanathan N. J. Chem. Soc., Perkin Trans.1 1974, 1161 - 25
Buckley TF.Rapoport H. J. Org. Chem. 1983, 48: 4222 - 26
Nordlander JE.Njoroge FG. J. Org. Chem. 1987, 52: 1627 - 27
Ihara M.Takino Y.Fukumoto K.Kametani T. Heterocycles 1989, 28: 63 - 28
Ihara M.Takino Y.Tomotake M.Fukumoto K. J. Chem. Soc., Perkin Trans 1 1990, 2287 - 29
Ihara M.Takino Y.Fukumoto K.Kametani T. Tetrahedron Lett. 1988, 29: 4135 - 30
Roush WR.Gillis HR.Ko AI. J. Am. Chem. Soc. 1982, 104: 2269 - 31
Evans DA.Chapman KT.Bisaha J. J. Am. Chem. Soc. 1988, 110: 1238 - 32
Herbert RB.Jackson FB.Nicolson IT. J. Chem. Soc., Perkin Trans. I 1984, 825 - 33
Bhakuni DS.Mangla VK. Tetrahedron 1981, 37: 401 - 34
Herbert RB. J. Chem. Soc., Chem. Commun. 1978, 794 - 35
Hedges SH.Herbert RB.Knagg E.Pasupathy V. Tetrahedron Lett. 1988, 29: 807 - 36
Cragg JE.Herbert RB.Jackson FB.Moody CJ.Nicoloson IT. J. Chem. Soc., Perkin Trans. 1 1982, 2477 - 37
Cragg JE.Hedges SH.Herbert RB. Tetrahedron Lett. 1981, 22: 2127 - 38
Cragg JE.Herbert RB. J. Chem. Soc., Perkin Trans. I 1982, 2487 - 39
Mangla VK.Bhakuni DS. Tetrahedron 1980, 36: 2489 - 40
Bhakuni DS.Gupta PK. Indian J. Chem. 1982, 21B: 393 - 41
Iida H.Watanabe Y.Tanaka M.Kibayashi C. J. Org. Chem. 1984, 49: 2412 - 42
Iida H.Kibayashi C. Tetrahedron Lett. 1981, 22: 1913 - 43
Iida H.Tanaka M.Kibayashi C. J. Chem. Soc., Chem. Commun. 1983, 271 - 44
Gellert E.Rudzats R.Craig JC.Roy SK.Woodard RW. Aust. J. Chem. 1978, 31: 2095 - 45
Suzuki H.Aoyagi S.Kibayashi C. J. Org. Chem. 1995, 60: 6114 - 46
Suzuki H.Aoyagi S.Kibayashi C. Tetrahedron Lett. 1995, 36: 935 - 47
Khatri NA.Schmittbenner HF.Shringarpure J.Weinreb SM. J. Am. Chem. Soc. 1981, 103: 6387 - 48
Bremmer ML.Khatri NA.Weinreb SM. J. Org. Chem. 1983, 48: 3661 - 49
Grieco PA.Parker DT. J. Org. Chem. 1988, 53: 3325 - 50
Nordlander JE.Payne MJ.Njoroge FG.Balk MA.Laikos GD.Vishwanath VM. J. Org. Chem. 1984, 49: 4107 - 51
Buckley TF.Rapoport H. J. Am. Chem. Soc. 1981, 103: 6157 - 52
Knudsen CG.Rapoport H. J. Org. Chem. 1983, 48: 2260 - 53
Maurer PJ.Takahata H.Rapoport H. J. Am. Chem. Soc. 1984, 106: 1095 - 54
Maurer PJ.Knudsen CG.Palkowitz AD.Rapoport H. J. Org. Chem. 1985, 50: 325 - 55
Pearson WH.Walavalkar R. Tetrahedron 1994, 50: 12293 - 56
Yerxa BR.Moore HW. Tetrahedron Lett. 1992, 33: 7811 - 57
Yerxa BR.Yang K.Moore HW. Tetrahedron 1994, 50: 6173 - 58
Cabri W.DeBernardinis S.Francalanci F.Penco S.Santi R. J. Org. Chem. 1990, 55: 350 - 59
Cuifolini MA.Roschangar F. J. Am. Chem. Soc. 1996, 118: 12082 - 60
Michael JP. Nat. Prod. Rep. 1998, 571 - 61
Liepa AJ.Summons RE. J. Chem. Soc., Chem. Commun. 1977, 826 - 62
Comins DL.Chen XH.Morgan LA. J. Org. Chem. 1997, 62: 7435 - 63
Comins DL.Morgan LA. Tetrahedron Lett. 1991, 32: 5919 - 64
Russel JH.Hunziker H. Tetrahedron Lett. 1969, 25: 4035 - 65
Straub CS.Padwa A. Org. Lett. 1999, 1: 83 - 66
Padwa A.Sheeham SM.Straub CS. J. Org. Chem. 1999, 64: 8648 - 67
Lebrum S.Couture A.Deniau E.Grandclaudon P. Tetrahedron 1999, 55: 2659 - 68
Zee-Cheng KY.Cheng CC. J. Pharm. Sci. 1970, 59: 1630 - 69
Rao KN.Bhattacharya RK.Venkatachalam SR. Chem.-Biol. Interact. 1997, 106: 201 - 70
Rao KN.Bhattacharya RK.Venkatachalam SR. Cancer Lett. 1998, 128: 183 - 71
Dolz H.Vazquez D.Jimenez A. Biochemistry 1982, 21: 3181 - 72
Söllhuber M.Grande MT.Trigo GG.❣ázquez D.Jimánez A. Curr. Microbiol. 1980, 4: 81 - 73
Al-Shamma A.Drake SD.Guangliardi LE.Mitscher LA.Swayze JK. Phytochemistry 1982, 21: 485 - 74
Bhutani KK.Sharma GL.Ali M. Planta Medica 1987, 532 - 75
Abe F.Iwase Y.Yamauchi T.Honda K.Hayashi N. Phytochemistry 1995, 39: 695 - 76
Honda K.Tada A.Hayashi N.Abe F.Yamauchi T. Experientia 1995, 51: 753 - 77
Shimizu T. Nogyo Oyobi Engei 1988, 63: 49 - 78
Tripathi AK.Singh D.Jain DC. Phytother. Res. 1990, 4(4): 144