Relevant bibliographies by topics / Aspidospermatane

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  1. Journal articles
  2. Dissertations / Theses

Academic literature on the topic 'Aspidospermatane'

Author: Grafiati
Published: 4 June 2021
Last updated: 5 February 2022

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Journal articles on the topic "Aspidospermatane"

1

Reina, Matías, Wilfredo Ruiz-Mesia, Lastenia Ruiz-Mesia, Rafael Martínez-Díaz, and Azucena González-Coloma. "Indole Alkaloids from Aspidosperma rigidum and A. schultesii and their Antiparasitic Effects." Zeitschrift für Naturforschung C 66, no. 5-6 (June 1, 2011): 225–34. http://dx.doi.org/10.1515/znc-2011-5-605.

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Five oxindole alkaloids, three plumerane-type alkaloids, subtype haplophitine, and one aspidospermatane-type alkaloid, subtype tubotaiwine, were isolated from the medicinal plants Aspidosperma rigidum and A. schultesii. One compound was identified as the transoid conformer of 18-oxo-O-methylaspidoalbine which was not previously described. The antiparasitic activity of all compounds against Trypanosoma cruzi and Leishmania infantum and their non-specific cytotoxicity against mammalian cells were also determined.
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2

Gan, Chew-Yan, Yun-Yee Low, Ward T. Robinson, Kanki Komiyama, and Toh-Seok Kam. "Aspidospermatan–aspidospermatan and eburnane-sarpagine bisindole alkaloids from Leuconotis." Phytochemistry 71, no. 11-12 (August 2010): 1365–70. http://dx.doi.org/10.1016/j.phytochem.2010.05.015.

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3

Kuehne, Martin E., and Feng Xu. "Total synthesis of strychnan and aspidospermatan alkaloids. 3. The total synthesis of (.+-.)-strychnine." Journal of Organic Chemistry 58, no. 26 (December 1993): 7490–97. http://dx.doi.org/10.1021/jo00078a030.

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4

Morita, Hiroshi, Kartini Ahmad, Yusuke Hirasawa, Alfarius Eko Nugroho, and A. Hamid A. Hadi. "NEW ASPIDOFRACTININE, ASPIDOSPERMATAN AND AKUAMILINE INDOLE ALKALOIDS FROM THE ROOTS OF KOPSIA SINGAPURENSIS RIDL." HETEROCYCLES 86, no. 2 (2012): 1611. http://dx.doi.org/10.3987/com-12-s(n)113.

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Kuehne, Martin E., Christopher S. Brook, Deborah A. Frasier, and Feng Xu. "Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 7. Total Syntheses of Lagunamine, Isolagunamine, Condylocarpine, and Isocondylocarpine." Journal of Organic Chemistry 60, no. 6 (March 1995): 1864–67. http://dx.doi.org/10.1021/jo00111a053.

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6

Hauduc, Clémence, and Guillaume Bélanger. "General Approach toward Aspidospermatan-Type Alkaloids Using One-Pot Vilsmeier–Haack Cyclization and Azomethine Ylide Cycloaddition." Journal of Organic Chemistry 82, no. 9 (April 18, 2017): 4703–12. http://dx.doi.org/10.1021/acs.joc.7b00345.

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7

Ahmad, Kartini, Yusuke Hirasawa, Alfarius Eko Nugroho, A. Hamid A. Hadi, and Hiroshi Morita. "ChemInform Abstract: New Aspidofractinine, Aspidospermatan and Akuamiline Indole Alkaloids from the Roots of Kopsia singapurensis Ridl." ChemInform 44, no. 17 (April 4, 2013): no. http://dx.doi.org/10.1002/chin.201317205.

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8

Parsons, Rodney L., Jeffrey D. Berk, and Martin E. Kuehne. "Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates." Journal of Organic Chemistry 58, no. 26 (December 1993): 7482–89. http://dx.doi.org/10.1021/jo00078a029.

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9

KUEHNE, M. E., and F. XU. "ChemInform Abstract: Total Synthesis of Strychnan and Aspidospermatan Alkaloids. Part 3. The Total Synthesis of (.+-.)-Strychnine (V)." ChemInform 25, no. 17 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199417241.

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10

Kuehne, Martin E., and Feng Xu. "Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 10. An Enantioselective Synthesis of (−)-Strychnine through the Wieland−Gumlich Aldehyde." Journal of Organic Chemistry 63, no. 25 (December 1998): 9427–33. http://dx.doi.org/10.1021/jo9813989.

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Dissertations / Theses on the topic "Aspidospermatane"

1

Hauduc, Clémence. "Vers la synthèse d’alcaloïdes de type aspidospermatane par une stratégie de séquence de cyclisation de Vilsmeier-Haack et de cycloaddition dipolaire-1,3 intramoléculaire d’ylure d’azométhine." Thèse, Université de Sherbrooke, 2017. http://hdl.handle.net/11143/10502.

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Récemment, notre groupe de recherche a mis au point une stratégie de synthèses de composés polycycliques impliquant une séquence de cyclisation de Vilsmeier-Haack et de cycloaddition dipolaire-1,3 intramoléculaire d’ylure d’azométhine. Afin de démontrer l’applicabilité de cette stratégie en synthèse totale, nous avons choisi les alcaloïdes de type aspidospermatane comme cible. Malgré qu’il existe plusieurs synthèses racémiques d’alcaloïdes dans cette famille, la version énantiosélective a été peu explorée. Nous avons d’abord exploré deux approches permettant l’installation du centre de chiralité qui contrôlera la stéréochimie absolue à tous les nouveaux centres chiraux générés lors de l’étape clé (chapitre 1). En dépit de l’obtention d’excès énantiomériques insatisfaisants, nous avons continué la synthèse de manière racémique afin d’optimiser la séquence réactionnelle. Ainsi, nous avons développé la synthèse du premier substrat d’étape clé qui, lorsque soumis aux conditions de cyclisation, n’a malheureusement pas mené au produit désiré. À partir de ce résultat, une optimisation du dipolarophile (chapitre 2), de l’ylure et du nucléophile a débuté. Différents substrats d’étape clé ont été synthétisés à partir de la séquence développée précédemment et ont été soumis aux conditions de cyclisation jusqu’à déterminer la bonne combinaison qui nous a permis d’obtenir le cycloadduit (chapitre 3). Pour finir, des travaux futurs sont suggérés afin d’installer de façon plus efficace le centre de chiralité et de terminer la synthèse énantiosélective des alcaloïdes de type aspidospermatane.
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2

Kokkonda, Praveen. "TOTAL SYNTHESIS OF STRYCHNOS AND ASPIDOSPERMATAN ALKALOIDS." Diss., Temple University Libraries, 2017. http://cdm16002.contentdm.oclc.org/cdm/ref/collection/p245801coll10/id/435652.

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Chemistry
Ph.D.
The Strychnos class of indole alkaloids contain a pyrrolo[2,3-d]carbazole ABCE tetracyclic framework. The second-generation ABCE tetracycle approach was employed in the total synthesis of (±)-20-epi-lochneridine and progress toward total synthesis of (±)-alstolucine B. The second-generation approach featured Mitsunobu activation of the hydroxyethyl group in a gramine intermediate followed by intramolecular aza-Baylis-Hillman reaction. The substrate for hydroboration was redesigned to (±)-18-desmethyl akuammicine (1,1-disubstituted double bond), since the hydroboration of trisubstituted alkenes afforded tertiary alcohol via Markovnikov addition. The key steps were n-Bu3SnH mediated cyclization reaction to accomplish D-ring, tert-butyl hypochlorite indoline oxidation, and anti-Markovnikov hydroboration to introduce a primary alcohol. The total syntheses of Strychnos-Strychnos type bis-indole alkaloids (−)-leucoridine A and C were accomplished from the biomimetic dimerization of (−)-dihydrovalparicine. En route to (−)-dihydrovialparicine, known alkaloids (+)-geissoschizoline and (−)-dehydrogeissoschizoline were also prepared from commercially available N-tosyl indole 3-carboxaldehyde. Key steps consisted of an in situ dimerization of (−)-dihydrovalparicine from (−)-1, 2-dehydrogeissoschizoline with trifluoroacetic acid in the presence of 4 Å molecular sieves. Acid mediated ring-opening of the indolenine in (−)-leucoridine A to afford (−)-leucoridine C. DFT calculations were employed to elucidate the mechanism of dimerization, which suggested that a stepwise aza-Michael/spirocyclization sequence was preferred over the alternate hetero Diels-Alder cycloaddition reaction. A novel domino Michael/Mannich [4+2] annulation method was applied for concise total synthesis of Aspidospermatan alkaloids (+)-20-epi-condyfoline and progress toward the total synthesis of (+)-condyfoline. The additional key steps consisted of a LiHMDS mediated cyclization to form D-ring, dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) mediated spirocyclization to form pentacyclic thioether and indoline oxidation with MnO2.
Temple University--Theses
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3

Dawood, Dawood Hosni. "Towards the synthesis of monoterpenoids indole alkaloids of the aspidospermatan and strychnan type." Thesis, Bordeaux 1, 2010. http://www.theses.fr/2010BOR14155/document.

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L'objectif de ce travail était d'accéder au squelette des alcaloïdes de type Aspidosperma et Strychnos à partir d'arylcyclohexa-2,5-diènes. Ces derniers sont d'abord synthétisés par réaction de Birch alkylante, puis ont été désymétrisés dans un premier temps par des réactions de Michael. Cette réaction fournit la cétone de Büchi, le noyau tétracyclique des alcaloïdes Aspidosperma en seulement en 6 étapes et un rendement global de 17%. Dans un second temps, la réaction d'amination oxydante catalysée par des métaux (Pd, Cu) a été développée. Cette réaction a permis un accès rapide au squelette pentacyclique d’aza-aspidospermanes et au squelette tétracycliques des alcaloïdes de type Strychnos. En parallèle, nous avons décrit une approche vers le squelette pentacyclique de la mossambine et la strychnine
The aim of this work was to access the skeleton of the Aspidosperma and the Strychnos alkaloids using arylcyclohexa-2,5-dienes as common synthetic precursors. Initially, these arylcyclohexadienes were synthesized through Birch reductive alkylation reactions. The desymmetrization of these cyclohexadienes was developed via the Michael addition reaction, providing the Büchi ketone, the tetracyclic core of Aspidosperma alkaloids, in only 6 steps and 17% overall yield. On the other hand, we described the oxidative amination reaction catalyzed by metals (Pd, Cu). The palladium oxidative amination reaction allowed a fast access to the pentacyclic framework of aza-aspidospermanes and the tetracyclic framework of the strychnos. In parallel, we have described an approach toward the pentacyclic skeleton of mossambine and strychnine
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