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

By Hans-Joachim Knölker

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

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Extra info for Alkaloid Synthesis (Topics in Current Chemistry)

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Upon treatment of 95 with a catalytic amount of p-TsOH in refluxing MeOH, cyclization occurred to give aminoacetal 96 as an allylation precursor. Treatment of aminoacetal 96 with allyltrimethylsilane in the presence of TiCl4 at low temperature gave 97 as the sole isomer at C-13, which would be formed by stereoselective allylation of the acyliminium intermediate. The NOE correlation between H-7 and the proton of the allyl group in 97 revealed that the allyl group was introduced in an axial orientation.

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.

34 Early Syntheses of Morphine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 Gates (1952) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Rice (1980) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42 Recent Syntheses of Morphine and/or Codeine . . . . . . . . . . . . . . . . . . .

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