Alkaloid Synthesis (Topics in Current Chemistry) by Hans-Joachim Knölker

By Hans-Joachim Knölker

Lycopodium Alkaloids: Isolation and uneven Synthesis, by way of Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, via Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, through Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, through Yasuyuki Kita and Hiromichi Fujioka.- artificial reports on Amaryllidaceae and different Terrestrially Derived Alkaloids, through Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by means of Ingmar Bauer and Hans-Joachim Knölker.-

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55 4 Medicinally Important Derivatives of Morphine . . . . . . . . . . . . . . . . . . . . . . 59 5 Conclusion and Outlook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 62 Abbreviations 2,4-DNPH BHT CSA DDQ DEAD DIAD DMAP DNsCl dpa dppf dppp EDCI IBX KHMDS LiHMDS MCPBA NaHMDS NBS PAD PPTS TBAF TCDI TFA 2,4-Dinitrophenylhydrazine Butylated hydroxytoluene Camphorsulfonic acid Dichloro dicyano benzoquinone Diethyl azodicarboxylate Diisopropyl azodicarboxylate 4-Dimethylaminopyridine 2,4-Dinitrobenzene-sulfonyl chloride Dibenzylidenacetone 1,10 -Bis(diphenylphosphino)ferrocene 1,3-Bis(diphenylphosphino)propane 1-Ethyl-3-(3-dimetylaminopropyl)carbodiimide 2-Iodoxybenzoic acid Potassium bis(trimethylsilyl)amide Lithium bis(trimethylsilyl)amide 3-Chloroperbenzoic acid Sodium bis(trimethylsilyl)amide N-Bromosuccinimide Potassium azodicarboxylate Pyridinium p-toluenesulfonate tetra-n-Butylammonium fluoride Imidazole 1,10 -thiocarbonyldiimidazole Trifluoroacetic acid 1 Introduction Morphine (1) and its congeners, codeine (2), thebaine (3), and oripavine (4), Fig.

Nishimura T, Unni AK, Yokoshima S, Fukuyama T (2011) Concise total synthesis of (+)lyconadin A. J Am Chem Soc 133:418–419 71. Beshore DC, Smith AB III (2007) Total syntheses of (+)-lyconadin A and (–)-lyconadin B. J Am Chem Soc 129:4148–4149 72. Bisai A, West SP, Sarpong R (2008) Unified strategy for the synthesis of the “miscellaneous” Lycopodium alkaloids: total synthesis of (Æ)-lyconadin A. J Am Chem Soc 130:7222–7223 73. Altman RA, Nilsson BL, Overman LE, Read de Alaniz J, Rohde JM, Taupin V (2010) Total synthesis of (+)-nankakurines A and B and (Æ)-5-epi-nankakurine A.

42 Recent Syntheses of Morphine and/or Codeine . . . . . . . . . . . . . . . . . . . . . . 1 Fukuyama (2006) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Hudlicky (2007) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3 Iorga and Guillou (2008) . . . . . . . . . . . . . . . . . . . .

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