By Mariko Kitajima, Hiromitsu Takayama (auth.), Hans-Joachim Knölker (eds.)
Lycopodium Alkaloids: Isolation and uneven Synthesis, by means of Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, through Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by means of Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, via Yasuyuki Kita and Hiromichi Fujioka.- man made stories 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, by means of Ingmar Bauer and Hans-Joachim Knölker.-
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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.
4 Cernuine and Related Alkaloids From L. cernuum collected in Okinawa Prefecture, cernuine (86) and a new alkaloid, cermizine C N-oxide (88), were isolated. Cernuine (86) is a representative of cernuane-type Lycopodium alkaloids. It was isolated by Marion and Manske in 1948 and its structure was elucidated by Ayer et al. in 1967 [45, 46] (Fig. 8). Its structure features a fused-tetracyclic ring system containing an aminal moiety that is rare among Lycopodium alkaloids. The relative configuration of 86 was determined from the coupling constants in the 1H NMR spectra, but its absolute configuration was deduced from CD spectra by comparison with those of related alkaloids.
46. 1]nonane. J Am Chem Soc 99:3427–3432 39. Brown HC, Jadhav PK (1984) B-Allyldiisocaranylborane: a new, remarkable enantioselective allylborating agent for prochiral aldehydes. Synthesis of homoallylic alcohols approaching 100% enantiomeric purities. J Org Chem 49:4089–4091 40. Jadhav PK, Bhat KS, Perumal PT, Brown HC (1986) Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess.
Alkaloid Synthesis by Mariko Kitajima, Hiromitsu Takayama (auth.), Hans-Joachim Knölker (eds.)