Iso‐<i>seco</i>‐tanapartholides: Isolation, Synthesis and Biological Evaluation

Makiyi, Edward F.; Frade, Raquel F. M.; Lébl, Tomáš; Jaffray, Ellis; Cobb, Susan E.; Harvey, Alan L.; Slawin, Alexandra M. Z.; Hay, Ronald T.; Westwood, Nicholas J.

doi:10.1002/ejoc.200901016

Cited by 28 publications

(30 citation statements)

References 26 publications

(19 reference statements)

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“…18 The spectroscopic data for compound 2 are identical to those described for the natural product isolated in 2008 10 and prepared in 2009. 16 Both previously described epoxides were reported with a different stereochemistry. This discrepancy was initially resolved by carrying out NMR NOESY studies on both isomers, with key correlations obtained for H-6/H-11/H-8β and H 3 -14/H-2α/H-2β/H-9α/H-9β for the natural product and H-6/H-11/H-8β and H 3 -14/H-2α for the isomer of the natural product.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Facile Preparation of Bioactive seco-Guaianolides and Guaianolides from Artemisia gorgonum and Evaluation of Their Phytotoxicity

et al. 2012

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Commercially available santonin was used to synthesize seven sesquiterpene lactones using a facile strategy that involved a high-yielding photochemical reaction. Three natural products from Artemisia gorgonum were synthesized in good yields, and in the case of two compounds, absolute configurations were determined from X-ray quality crystals. The structures previously reported for these compounds were revised. Sesquiterpene lactones were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species. seco-Guaianolide (4) showed higher phytotoxic activities than the known herbicide Logran. This high activity could be due to the presence of a cyclopentenedione ring. These results suggest that compound 4 should be involved in defense of A. gorgorum, displaying a wide range of activities that allow proposing them as new leads for development of a natural herbicide model with a seco-guaianolide skeleton.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Facile Preparation of Bioactive seco-Guaianolides and Guaianolides from Artemisia gorgonum and Evaluation of Their Phytotoxicity

et al. 2012

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“…Dazu zählen die Guaiane (+)-Achillin (140), [201] (À)-Estafiatin (141), [202] (+)-Pachydictyol A (142), [203] (À)-Oxoisodehydroleucodin, [204] (+)-Jalcaguaianolid, [205] 1a,7a,10aH-Guaian-4,11-dien-3-on, [206] Hydrocolorenon, [206] Plagiochilin N [207] sowie beide Epimere der Iso-seco-tanapartholide. [208] In deutlich besseren Ausbeuten verliefen die photochemischen Umlagerungen von Santonin-Derivaten, in denen zunächst das Lacton geöffnet wurde. Auf diese Weise wurden mehrere 4a-Hydroxy-8,12-guaianolide [209] sowie (+)-Podoandin und (+)-Zedolacton A synthetisiert.…”

Section: Umlagerungen Von Kreuzkonjugierten Cyclohexadienonenunclassified

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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“…[45] A key step was the late-stage oxidative cleavage reaction, which was carried out in the absence of protecting groups to give the natural products directly (Scheme 12). In 2009 Hay, Westwood, and co-workers reported the isolation, synthesis, and biological evaluation of iso-seco-tanapartholides 68 and 69.…”

Section: Eudesmanolide Strategiesmentioning

confidence: 99%

Trends in the Synthesis and Functionalization of Guaianolides

2015

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Guaianolides constitute a large and diverse group of biologically active sesquiterpenes. Guaianolide and seco‐guaianolides can also be used as, for example, scaffolds for the development of new active molecules that are readily accessible by synthetic methods. Nevertheless, these lactones often have complex structures that make their synthesis difficult. The aim of this microreview is to provide an overview of the developments in guaianolide synthesis by the two major synthetic strategies: semi‐synthesis and total synthesis. Partial and total syntheses of guaianolides are described, with particular emphasis placed on the methods reported in the last decade. The methods discussed include rearrangements, cycloadditions, ring‐closing metathesis, the use of transition‐metal catalysts, photochemical reactions, and other recently developed techniques as key steps.

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Iso‐seco‐tanapartholides: Isolation, Synthesis and Biological Evaluation

Cited by 28 publications

References 26 publications

Facile Preparation of Bioactive seco-Guaianolides and Guaianolides from Artemisia gorgonum and Evaluation of Their Phytotoxicity

Facile Preparation of Bioactive seco-Guaianolides and Guaianolides from Artemisia gorgonum and Evaluation of Their Phytotoxicity

Photochemische Reaktionen als Schlüsselschritte in der Naturstoffsynthese

Trends in the Synthesis and Functionalization of Guaianolides

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