Asymmetric Total Synthesis of Antitumor Styryl Lactones and Related Natural Products

杨智才,; 周维善,

doi:10.3987/rev-96-487

Cited by 34 publications

(6 citation statements)

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“…[36] Beispielhaft erwähnt sei die von Cava et al gewählte Route zur Synthese des (AE )-Dicentrins (30). [37] Durch Bischler-Napieralski-Reaktion wurde aus dem Amid [37] (AE )-Aporphin, [38] (AE )-Nuciferin, [38,39] (AE )-Glaucin, [39] (AE )-Cassamedin, [40] (AE )-Sinomendin, [41] (AE )-Elmerrillicin, [42] Pontevedrin, [43] Cepharadion B [44] und (AE )-Goudotianin. [45] In ähnlicher Weise lassen sich auch Alkaloide herstellen, in denen das Stickstoffatom kein Substituent des Stilbenchromophors ist.…”

Section: Aufsätzeunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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Photochemische Reaktionen bereichern in signifikanter Weise das Repertoire zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen und machen ungewöhnliche, auf herkömmlichem Weg nicht erhältliche Molekülgerüste zugänglich. In diesem Aufsatz werden die wichtigsten Umsetzungen der Photochemie vorgestellt, die auf breiter Front Einzug in die Naturstoffsynthese gehalten haben. Beispielhaft werden einzelne Totalsynthesen diskutiert, wobei besonderes Augenmerk auf den photochemischen Schlüsselschritt sowie dessen Stereoselektivität gerichtet ist. Dabei wird das photochemisch erzeugte Molekül in Relation zur Struktur des Naturstoffs gebracht, und Folgereaktionen werden, wo notwendig, illustriert und klassifiziert.

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Section: Aufsätzeunclassified

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

2011

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“…The anti-insect activity of tetranortriterpenoids has been investigated extensively, with particular attention focused on the ring-cleaved example, azadirachtin. , In contrast, less is known about the activity of compounds in the mexicanolide class, such as 1 − 4 , with the exception of a series of derivatives (humilinolides A−D), which are insecticides and developmental inhibitors of the European corn borer ( Ostrinia nubilalis Hübner) 5d. In addition to their association with leaf rejection, the concentration of 1 − 4 in C. odorata was found to vary with respect to tree genotype; however, the concentration of the active compounds 1 − 3 was greater than that of the inactive compound 4 in all of the leaf material sampled .…”

Section: Resultsmentioning

confidence: 99%

“…C. odorata is characterized chemically by the presence of tetranortriterpenoids (limonoids), , a group of compounds that exhibit a wide variety of biological properties. These include insect antifeedant activity and toxicity, and antimalarial, antibacterial, and antifungal activity. Phytochemical studies of timber trees in Meliaceae have focused almost exclusively on the bark and heartwood, rather than leaves or leaf shoots.…”

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Four New Tetranortriterpenoids from Cedrela odorata Associated with Leaf Rejection by Exopthalmus jekelianus

1999

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Four new tetranortriterpenoids, 3-deoxo-3beta,8beta-epoxy-6, 14alpha-dihydroxy-8,14-dihydromexicanolide (cedrodorin, 1); 3-deoxo-3beta,8beta-epoxy-6-acetoxy-14alpha-hydroxy-8, 14-dihydromexicanolide (6-acetoxycedrodorin, 2); 3-deoxo-3beta, 8beta-epoxy-6-deoxy-9alpha,14alpha-dihydroxy-8, 14-dihydromexicanolide (6-deoxy-9alpha-hydroxycedrodorin, 3); and 3-deoxo-3beta,8beta-epoxy-6,9alpha,14alpha-trihydroxy-8, 14-dihydromexicanolide (9alpha-hydroxycedrodorin, 4), have been isolated from the leaves of Cedrela odorata by HPLC. Their molecular structures were determined by 1D and 2D NMR. Three of the compounds are associated with leaf rejection by the polyphagous, folivorous weevil, Exopthalmus jekelianus. The importance of these compounds as insect deterrents in C. odorata, and their potential value in the selection of insect-resistant clones for timber plantations is discussed.

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“…Die nichtoxidative [6π]‐Photocyclisierung ergab das gewünschte Phenanthren 29 , das anschließend reduktiv in den Naturstoff 30 umgewandelt werden konnte. Zu den weiteren Aporphinen, die durch ähnliche Routen mit einer [6π]‐Photocyclisierung als Schlüsselschritt hergestellt wurden, gehören Cassameridin,37 (±)‐Aporphin,38 (±)‐Nuciferin,38, 39 (±)‐Glaucin,39 (±)‐Cassamedin,40 (±)‐Sinomendin,41 (±)‐Elmerrillicin,42 Pontevedrin,43 Cepharadion B44 und (±)‐Goudotianin 45…”

Section: Photocyclisierungenunclassified

Book review

Larsson¹

2001

Int J of Quantum Chemistry

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Volume 1 has the subtitle Basic Problems and ModelSystems and consists of five parts. The first two parts deal with density matrices and electron correlation. Kozmutza, Kapui, and Udvardi have carried out an interesting study of transferability of electron correlation effects in a localized representation. Examples are taken from CH and CC bonds in polyenes and noble-gas clusters. Most of the other chapters consist of improved calculations of correlation effects on various properties. The last chapter, by Kaplan et al., is different since it describes calculations on a cluster of a superconducting CuO system. Here the chances to obtain a converged and meaningful end result are not great, but the authors make a brave and far-reaching attempt using second-order Møller-Plesset (MP2) method with careful inclusion of the Madelung corrections. Three copper atoms are included, but the two outermost ones are missing one of their oxygen neighbors. The hole states, due to the missing electron in the Cu 3d subshell, is localized on different atoms and in different orbitals, depending on calculation method. This confusing picture seems to be unavoidable and has been seen before in studies by Broer and Nieuwpoort and other works cited in the Kaplan paper.Part III, containing "Relativistic Formulations," is impressive in both width and depth. Particularly the first two chapters, written by Kaldor and Eliav and by Karwowski et al., are interesting reading and give a good summary of the field.

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Asymmetric Total Synthesis of Antitumor Styryl Lactones and Related Natural Products

Cited by 34 publications

References 0 publications

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Four New Tetranortriterpenoids from Cedrela odorata Associated with Leaf Rejection by Exopthalmus jekelianus

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