Further studies on lemobiline: Partial synthesis of (−)Lemobiline and its conversion to (−)Ravenoline
01 Jan 1971-Tetrahedron Letters (Pergamon)-Vol. 12, Iss: 28, pp 2683-2686
About: This article is published in Tetrahedron Letters.The article was published on 1971-01-01. It has received 4 citations till now.
TL;DR: It is shown that, from the alkaloid data available, Engler's classification of the major sub-families Rutoideae and Toddalioideae is untenable and an hypothesis for the phylogeny of the Rutales, based on the distribution of alkaloids and other secondary metabolites, is proposed.
Abstract: The biosynthesis of the alkaloids of the Rutaceae and its relevance to their systematic value is discussed. The alkaloids are divided into groups of potential systematic significance and their distribution reviewed and analysed with respect to presently accepted taxonomic classifications for the family. It is shown that, from the alkaloid data available, Engler's classification of the major sub-families Rutoideae and Toddalioideae is untenable. An hypothesis for the phylogeny of the Rutales, based on the distribution of alkaloids and other secondary metabolites, is proposed.
••01 Jan 1988
TL;DR: A detailed review of quinoline alkaloids, their structure, preparation and biosynthesis can be found in this article, along with a discussion of 3-prenyl-2-quinolinones.
Abstract: Publisher Summary The quinoline alkaloids are derived from anthranilic acid. More than 80 new quinoline alkaloids have been isolated, a new group, the dimeric quinolinones, has been discovered, and considerable advances have been made in the synthesis of the alkaloids. Spectroscopic methods continue to be crucial in the elucidation of the structures of quinoline alkaloids. This chapter reviews various quinoline alkaloids, their structure, preparation and biosynthesis. Derivatives of 4-hydroxy-2-quinolinone are discussed along with 3-prenyl-2-quinolinones, derived by C-allylation of intermediate 4-hydroxy-2-quinolinone. The 3-prenyl-2-quinolinones occupy a central position in the sequence; oxidative cyclization leads to dihydropyranoquinolines or dihydrofuroquinolines exemplified by isobalfourodine and platydesmine, respectively; dehydration of the latter compounds may be responsible for example, for the formation of terminal olefins. On the other hand, oxidation of 3-prenyl-2-quinolinones to a diene 4 provides the opportunity for intramolecular cyclization to the large group of dimethylpyranoquinolinones, and intermolecular addition to give dimeric quinolinone alkaloids.
••01 Jan 1979
TL;DR: The application of spectroscopic methods for the elucidation of the structures of quinoline alkaloids has developed to the point where the constitutions of many new alkaloids have been established solely by UV, IR, NMR, and mass spectrometry as mentioned in this paper.
Abstract: Publisher Summary The application of spectroscopic methods for the elucidation of the structures of quinoline alkaloids has developed to the point where the constitutions of many new alkaloids have been established solely by UV, IR, NMR, and mass spectrometry. The NMR spectra of quinoline alkaloids have been discussed and the application of mass spectrometry has also been reviewed. These schemes summarize NMR data for a selection of typical quinoline alkaloids. In discussing structure work, spectroscopic data will be given only when they are of special significance. Concise general reviews of quinoline alkaloids appeared in 1970 and in 1974, and annual coverage is provided by the Chemical Society, London. A review listing in convenient form the occurrence of rutaceous alkaloids up to April 1973 has been published. A valuable account of the synthesis of 2,4-dioxyquinoline alkaloids is now available. This chapter presents a review that includes the work published during the period 1966-mid 1976.
••01 Jan 2015
TL;DR: Alkaloids are structurally most diversified natural products as mentioned in this paper, and they offer simple (e.g., in Chaps. 16, 22) to very complex structural patterns.
Abstract: Alkaloids are structurally most diversified natural products. They offer simple (e.g., in Chaps. 16– 22) to very complex structural patterns (e.g., in Chaps. 27 and 28). Their biological activities claim a special attention for drug discovery (Chap. 33). Some representative members of a few different classes of alkaloids have been included and discussed in Chaps. 15– 29. To illustrate further structural diversifications several examples of alkaloids (Fig. 30.1) not included in earlier Chapters are cited in this chapter with references. The stereostructures of these alkaloids have been settled in the usual way by suitable combinations of the following: degradation, spectral analysis, synthesis, chemical correlations, applications of some rules (e.g., Prelog’s rule, Bredt’s rule, etc.), and occasionally by ORD studies and X-ray crystallography. A plethora of alkaloids with diversified structural patterns belonging to different classes appearing in the literature during 1960s  and till 1988  have been compiled with some leading references concerning their isolation/structure/stereochemistry/synthesis. Quite a number of review articles on the uses of heterocycles in the synthesis of alkaloids have collectively appeared in an edited book in 2011 . They display wide structural variations of alkaloids.
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