Alkaloids and Derivatives

Cinchona alkaloids such as quinine and quinidine are readily available chiral compounds. Prelog and Wilhelm reported in 1954 cinchona alkaloid-catalyzed 

Hermann and Wynberg reported the M ichael reaction of a (3-kcto ester with methyl vinyl ketone under the influence of the quinine 3b to give the Michael adduct with 76% ee (Equation 10.10) [24], 

Hatakeyama and co-workers reported the highly enantioselective Baylis-Hillman reaction of 1,1,1,3,3,3-hexafluoroisopropyl acrylate with an aldehyde, which is catalyzed by the cinchona alkaloid catalyst 4 that was readily available from (+ )-quinidine (Equation 10.11) [25], 

Deng reported the cinchona alkaloid-catalyzed desymmetrization of meso and achiral cyclic anhydrides by alcoholysis [26]. 

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Rice, K.C. (1980) Synthetic Opium Alkaloids and Derivatives. A Short Total Synthesis of (ib)-Dihydrothebainone, ( )-Dihydrocodeinone, and ( )-Nordihydrocodemone as an Approach to a Practical Synthesis of Morphine, Codeine, and Congeners. Journal of Organic Chemistry, 45, 3135-3137. 

Treatment of cells with vinblastine or vincristine can result in the formation of paracrystals, complexes containing the alkaloid molecules and tubulin dimers in a 1 1 ratio. Paracrystal formation in neuronal tissue of a freshwater snail has been proposed as a model for the neurotoxic effects of Catharanthus alkaloids and derivatives 44). Vincristine is approximately 10-fold more active than vinblastine as an inducer of paracrystal formation when snail neuronal tissue is treated with high concentrations (150 lM) of the alkaloids. 

Dams et al. [19] determined seven different opium alkaloids and derivatives in seized heroin using fast LC-MS analysis. Analytes were separated in 5 min on a monolithic silica column with a gradient elution system and an optimized flow of 5 mL/min. Detection was carried out using a sonic spray ion source [20] a modified ESI source were ionization is achieved using a nebulizer gas at sonic speed instead of applying an electrical field. 

Ergot alkaloids and derivatives Ergotamine Lysergic acid diethylamide (LSD) 2-Bromolysergic acid amide (BOL) 1-3 mg/day, 0.25-0.5 mg SC/IM... 

Opium alkaloids and derived phenanthrene alkaloids codeine, morphine, (Avinza, Kadian, MSContin, Roxanol), hydromorphone (Dilaudid), oxymorphone (Numorphan), oxycodone (dihydroxycodeinone, a component of Oxycotin, Oxydose, Oxyfast, Percodan, Percocet, Roxicodone, Tylox)... 

Physical and spectral properties of samandarine alkaloids are presented in Table II. Mass spectra of various samandarine alkaloids and derivatives have been presented 38-43). Fragments of C4H8NO (m/z 86) and C4H7NO+ (m/z 85) are typical of oxazolidine-containing samandarine alkaloids. Infrared spectra of various samandarine alkaloids have been published 33,34,43-46 and references therein). Proton magnetic resonance spectra for samandarone, samandenone, and cycloneosamandione have been presented 38,40,41). Samandarine, samandarone, and... 

Figure 3. Polyhydroxylated pyrrolidine alkaloids and derivatives isolated from Broussonetia kazinoki.

The retention times of the non-ester alkaloids and derivatives are listed in Table 4.1 and those of the esters with monocarboxylic acids in Table 4.2. In Table 4.3 the retention times of the macrocyclic diesters are given. 

RETENTION TIMES, tR, OF NON-ESTER PYRROLIZIDINE ALKALOIDS AND DERIVATIVES ON A 4 % SE-30 PACKED COLUMN ON GAS CHROM P AT 140°C1... 

GAS CHROMATOGRAM OF TROPINE ALKALOIDS AND DERIVATIVES AS TRIMETHYLSILYL DERIVATIVES32... 

As in the case of microbially derived anticancer agents (Section IV.E.2.), interested readers can consult the information on podophyUotoxin and derivatives, the vinca alkaloids and derivatives, and camptothecin and derivatives in the recent volume edited by the authors of this chapter. 

Mattocks AR. Relation of structural features to pyrrolic metabolites in livers of rats given pyrrolizidine alkaloids and derivatives. Chem Biol Interact 1981 35 301-10. 

Physical and Spectroscopic Data of Monoterpene Pyridine Alkaloids and Derivatives 1... 

Maulding HV and Zoglio MA, Physical chemistry of ergot alkaloids and derivatives. I. Ionization ccHistants of several medicinally active bases, /. Pharm. Set, 59, 700-701 (1970). NB Solubility increased by complexaticHi with 7-p-hydroxypropyltheophylline (7HPT) and the apparent pKa values extrapolated to [7HPT] = 0. Solutions were titrated with carbonate-free KOH solution. See mettiysergide for further details. 

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