Of morphine alkaloids

Zezula, J. Hudlicky, T. (2005) Recent Progress in the Synthesis of Morphine Alkaloids. Synlett, 388 05. 

LongMT et al. (1995) Transformations of morphine alkaloids by Pseudomonas putida MIO. Appl Environ Microbiol 61(10) 3645-3649... 

The hasubanan alkaloids had been discussed as a subgroup of morphine alkaloids in Volume 13 of this treatise (/) until the succeeding review was published in 1977 (2) the two reviews cover the literature up to 1976. Since the... 

The plan for a tandem cyclization as the key step in the synthesis of morphine alkaloids has been successfully performed [95]. Three examples are given in Scheme 7.10. Specifically, the initially formed aryl radical, generated by bromine abstraction from compound 74, underwent a tandem cyclization to construct the desired carbocyclic skeleton. Depending on the nature of the Z substituent to the double bond, the product radicals either abstracted hydrogen from silane (Z = C02Me or CN) or eliminated thiyl radical (Z = SPh). 

Bruce, N. et al. (1995). Engineering pathways for transformations of morphine alkaloids. Trends Biotechnol. 13,... 

Morgan, D.J., et al. 1992. Prolonged release of morphine alkaloid from a lipophilic suppository base in vitro and in vivo. Int J Clin Pharmacol Ther Toxicol 30 576. 

The change from morphine to 3,6-diacetylmorphine is accompanied by a low frequency shift of C(7) (S 133-43 to 129-24) due to the y-effect of the acetoxyl group. C(10) appears at unusually low frequency (y-effects from C(8), C(16), and V-methyll in a number of morphine alkaloids with the exception of thebaine (cf. d 20-20 in morphine, 29-5 in thebaine) in which the gauche relationship between C(10) and C(8),... 

J. H. Knox and J. Jurand, Separation of morphine alkaloids heroin, methadone and other drugs by ion-exchange chromatography, J. Chromatogr., 52 398 (1973). 

I3C Chemical Shifts of Morphine Alkaloids and Model Compounds... 

Thioaldehydes as heterodienophiles in the synthesis of morphine alkaloids 93PS(74)17. 

Varieties of Papaver somniferum with varying content of morphine alkaloids have been studied, and varieties having a genetically governed low alkaloid content have been identified.143 The dynamics of the variation of amount of morphine and codeine present in P. somniferum with time of harvesting of the capsule have been studied.144 The thebaine content of P. bracteatum in relationship to plant development has been studied, and strains have been isolated from which may be obtained a dried latex that contains >55% thebaine, corresponding theoretically to a yield of 58 kg ha-1 or approximately 50 kg ha-1 from harvested capsule.145... 

Oripavine 3-ethyl ether (38), an unnatural analogue of thebaine (35), was found to be metabolized to morphine 3-ethyl ether and to morphine (36). The efficiency of the conversion was comparable to that of natural biosynthesis. (For an examination of other unnatural compounds as substrates for the enzymes of the biosynthesis of morphine alkaloids, see Vol. 4, p. 15.)... 

Irrespective of the exact timing of the isolation of morphine, alkaloids were discovered at an ever increasing rate from plant sources over the next... 

K. Goto, Sinomenine, an Optical Antipode of Morphine Alkaloids, p. 96, Kitasato Institute,... 

K W Bentley, The Chemistry of Morphine Alkaloids, Clarendon Press, Oxford (1954)... 

The skeleton of morphine alkaloids has been synthesized by intramolecular coupling (equation 37). ... 

The medical uses of morphine alkaloids have been known at least since the seventeenth century, when mide extracts of the opium poppy. Papaver somniferum, were used for the relief of pain. Morphine was the first pure alkaloid to be isolated from the poppy, but its clgsc relative, codeine, atso occurs naturally. Codeine, which is simply the rtethyl ether of morphine and is convert to morphine in the body, is ufed in preacription cough medicines and as an analgesic. Heroin, another close relative of morphine, does not occur naturally but is synlhesiiced by dlacotylalioii nf morphine. 

Rimazolium is a non-narcotic analgesic that strongly potentiates the analgesic and antagonizes the respiratory depressant effect of morphine alkaloids in animals and prevents the development of tolerance to morphine in animals and humans (1). Although rimazohum is not a new drug, experience with it is very hmited. 

An efficient synthesis of the thebaine analogue (158), as outlined in Scheme 13, in which the nitrogen atom is translocated from C(17) to the 16-position has been reported.161 It was converted into the Bentley adduct (159) by successive Diels-Alder and Grignard reactions. Further work on the Diels-Alder reactions of morphine alkaloids is expected for example, the enamine (160) has been prepared specifically for this purpose.162... 

In this chapter, a brief overview of the state of the art of morphine research is provided along with a detailed review of the several total syntheses that have materialized to date. Some approaches to the general skeleton of morphine alkaloids are also presented in order that such attempts may be put in perspective with the completed studies. Omitted from the review are the syntheses of derivatives and pharmaceuticals resulting from manipulation of the natural product itself. The authors would hope that the comparison of total synthetic approaches will serve to inspire the creative reader and lead to an efficient and artistic attainment of the title compound in the future. The literature in this area has been reviewed through the end of 1994. 

The tandem radical cyclization synthesis of morphine alkaloids Fokas, Demosthenes... 

A study of the phenolic oxidative coupling reaction in the synthesis of morphine alkaloids. An approach to the asymmetric synthesis of codeine... 

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