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Bücher Englische Bücher Wissen & Bildung Naturwissenschaft, Medizin, Informatik, Technik Chemie Organische Chemie Studies towards the synthesis of raputindole A, a dimeric indole alkaloid from the rutaceous tree Raputia simulans
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Studies towards the synthesis of raputindole A, a dimeric indole alkaloid from the rutaceous tree Raputia simulans
Nils Marsch (Broschiert, Englisch)
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Beschreibung
In 2010, the raputindoles A-D were isolated from the rutaceous tree Raputia simulans Kallunki from tropical South America. These bisindoles bear a unique cyclopentene ring anellated to the 5,6-position of one of the indole core structures. This dissertation describes the development of a synthetic approach towards raputindole A, starting from a general precursor leading to small molecule building… blocks and bisindole precursors. 6-Iodoindole was synthesized via Batcho-Leimgruber indole synthesis to serve as a precursor for Pd-mediated reactions. A variety of 6-substituted indoles has been synthesized and subjected to cytotoxicity tests. Two natural products from Monodora angolensis and Monodora tenuifolia showed the highest activity among the synthesized indoles. Propargyl alcohol indoles and bisindoles have been synthesized from both 6-iodoindole and a more advanced 5,6-functionalized indole. A Meyer-Schuster rearrangement was carried out on propargyl alcohols to yield alpha,beta-unsaturated ketones which were subjected to various conditions in order to achieve cyclization to the core structure of raputindole A. samarium diiodide induced dimerization of indoles with alpha,beta-unsaturated ketone substructures led to cyclopentyl bisindoles with an unusual stereochemistry. The natural product indiacen B from the myxobacterium Sandaracinus amylolyticus was synthesized. Indiacen B exhibits antimicrobial activity against Gram-positive and Gram-negative bacteria and the fungus Mucor hiemalis. A five step sequence yielded the natural product in 5% overall yield. The antimicrobial activity of the natural product against Nocardioides simplex, Mycobacterium diernhoferi, Chromobacterium violaceum and Mucor hiemalis was confirmed. Dieses Produkt haben wir gerade leider nicht auf Lager.
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Bis zu 50 % günstiger als neu
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Technische Daten
Erscheinungsdatum
27.08.2015
Sprache
Englisch
EAN
9783843922296
Herausgeber
Dr. Hut
Serien- oder Bandtitel
Organische Chemie
Sonderedition
Nein
Autor
Nils Marsch
Seitenanzahl
191
Einbandart
Broschiert
Schlagwörter
indole alkaloids, Raputia simulans, raputindole A
Thema-Inhalt
P - Mathematik und Naturwissenschaften
PNN - Organische Chemie
PN - Chemie
Höhe
210 mm
Breite
14.8 cm
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