- Studies on the stereostructure of eudesmanolides from Umbelliferae: Total synthesis of (+)-decipienin A
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The first total synthesis of (+)-decipienin A has been achieved in 4% overall yield in seven steps from (+)-dihydrocarvone, thus confirming the stereostructure proposed by Holub et al. (Holub, M.; Budesinsky, M. Phytochemistry 1986, 25, 2015-2026) for thi
- Macías, Francisco A.,Aguilar, José María,Molinillo, José María G.,Rodríguez-Luís, Francisco,Collado, Isidro G.,Massanet, Guillermo M.,Fronczek, Frank R.
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- Asymmetric synthesis of 3β-angeloyloxy-4β-hydroxyeudesman-8-one, purported sesquiterpene from pluchea quitoc
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Asymmetric synthesis of 3β-angeloyloxy-4βhyroxyeudesman-8-one, purported isolated from Pluchea quitoc was carried out. The synthesis exemplifies a flexible approach, which is applicable to the preparation of a number of eudesmane natural products. The res
- Muri, Estela,Kanazawa, Alice,Barreiro, Eliezer,Greene, Andrew E.
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- Enantioselective synthesis of (+)-decipienin A
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The enantioselective synthesis of (+)-decipienin A has been carried out. The oxidation of 7-epi-cyperone 2 with molecular oxygen in the presence of methanolic KOH provides de C-6-hydroxylated derivative in quantitative yield. The oxidation of glycols 5a t
- Aladro, F.Javier,Guerra, Francisco M,Moreno-Dorado, F.Javier,Bustamante, Jesús M,Jorge, Zacarías D,Massanet, Guillermo M
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- Synthesis of mono- and sesquiterpenoids; XXIV: (-)-Homogynolide A, an insect antifeedant isolated from Homogyne alpina
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(-)-Homogynolide A (1), an insect antifeedant isolated from Homogyne alpina (Compositae), was synthesized from (1R,4S,6S)-6-hydroxy-1-methylbicyclo[2.2.2]octan-2-one (7), which was readily prepared by the yeast reduction of the corresponding prochiral β-d
- Mori,Matsushima
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- Semisynthesis of (+)-angeloyl-gutierrezianolic acid methyl ester diterpenoid
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This paper describes the use of zamoranic acid in the first semisynthesis of the furolabdane (+)-angeloyl-gutierrezianolic acid methyl ester diterpenoid, which also establishes the absolute configuration of the natural product. Direct deconjugation of Δs
- Marcos,Benéitez,Moro,Basabe,Díez,Urones
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- A METHOD OF PRODUCING INGENOL-3-ANGELATE
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The present invention relates to methods of producing ingenol-3-angelate (I) from ingenol (II). Formula (I) and (II). Furthermore, the invention relates to intermediates useful for the synthesis of ingenol-3-angelate (I) from ingenol (II) and to methods of producing said intermediates.
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Page/Page column 36
(2012/02/05)
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- Semisynthesis of ingenol 3-angelate (PEP005): Efficient stereoconservative angeloylation of alcohols
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A high-yielding method was developed for the preparation of ingenol 3-angelate (PEP005, ingenol mebutate) via the corresponding 5,20-acetonide without concomitant isomerization of the angelate (Z-form) to the corresponding tiglate (E-form). The general sc
- Liang, Xifu,Grue-Sorensen, Gunnar,Petersen, Anders Klarskov,H?gberg, Thomas
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supporting information
p. 2647 - 2652
(2013/01/15)
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- Asymmetrie total syntheses of (-)-renieramycin M and G and (-)-jorumycin using aziridine as a lynchpin
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"Chemical Equation Presented" By exploring the triple reactivity of two aziridines and double nucleophilicity of two aromatics, convergent and versatile syntheses of the above four natural products were developed.
- Wu, Yan-Chao,Zhu, Jieping
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supporting information; experimental part
p. 5558 - 5561
(2010/02/28)
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- Synthesis and cytotoxic evaluation of some cribrostatin-ecteinascidin analogues
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Analogues of cribrostatin IV (1) and the potent antineoplastic agent ecteinascidin 743 (2) have been synthesized. The cytotoxic activity of these compounds (5, 14, 20) has been determined, and the cyanoamine-cribrostatin analogue (14) exhibits a 20-fold improvement with regard to the natural product 1.
- Wright, Benjamin J. D.,Chan, Collin,Danishefsky, Samuel J.
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experimental part
p. 409 - 414
(2009/04/05)
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- Total synthesis of thapsigargin, a potent SERCA pump inhibitor
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The enantioselective total synthesis of thapsigargin, a potent, selective inhibitor of the Ca2+ pump SERCA, is described. Starting from ketoalcohol 8, key steps involve regioselective introduction of the internal olefin at C4-C5, judicious protecting group choice to allow chelation-controlled reduction at C3, and chemoselective introduction of the angelate ester function at C3-0. A selective esterification approach completes the total synthesis in a total of 42 steps and 0.61% overall yield (88.6% average yield per step).
- Ball, Matthew,Andrews, Stephen P.,Wierschem, Frank,Cleator, Ed,Smith, Martin D.,Ley, Steven V.
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p. 663 - 666
(2008/02/05)
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- Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition
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Herein we describe the total synthesis of five guaianolide natural products: thapsigargin. thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for further investigation of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.
- Andrews, Stephen P.,Ball, Matthew,Wierschem, Frank,Cleator, Ed,Oliver, Steven,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Huenger, Udo,Smith, Martin D.,Ley, Steven V.
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p. 5688 - 5712
(2008/02/13)
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- Enantioselective total synthesis of the highly oxygenated 1,10-seco-eudesmanolides eriolanin and eriolangin
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Sultones of swing: A sultone served as the key intermediate in the first enantioselective total syntheses of the bioactive title compounds (see scheme), the absolute configuration of which is now established. Starting from 2-bromo-1-(2-furyl)ethanone, 24
- Merten, Joern,Froehlich, Roland,Metz, Peter
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p. 5991 - 5994
(2007/10/03)
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- Syntheses of the antibiotic alkaloids renierone, mimocin, renierol, renierol acetate, renierol propionate, and 7-methoxy-1,6-dimethylisoquinoline-5, 8-dione
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The total synthesis of renierone, mimocin, renierol, renierol acetate, renierol propionate, and 7-methoxy-1,6-dimethylisoquinoline-5,8-dione was successfully achieved by the regioselective oxidation of 5-oxygenated isoquinoline. The synthetic method of the 5-oxygenated isoquinoline is based on the thermal electrocyclic reaction of 1-azahexatriene system involving the benzene 1,2-bond.
- Kuwabara, Nagako,Hayashi, Hiroyuki,Hiramatsu, Noriko,Choshi, Tominari,Kumemura, Teppei,Nobuhiro, Junko,Hibino, Satoshi
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p. 2943 - 2952
(2007/10/03)
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- First comprehensive bakkane approach: Stereoselective and efficient dichloroketene-based total syntheses of (±)- and (-)-9-acetoxyfukinanolide, (±)- and (+)-bakkenolide a, (-)-bakkenolides III, B, C, H, L, V, and X, (±)- and (-)-homogynolide A, (±)-homogynolide B, and (±)-palmosalide C
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Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro β-methylene-γ-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol isomers.
- Brocksom, Timothy J.,Coelho, Fernando,Depres, Jean-Pierre,Greene, Andrew E.,Freire de Lima, Marco E.,Hamelin, Olivier,Hartmann, Benoit,Kanazawa, Alice M.,Wang, Yanyun
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p. 15313 - 15325
(2007/10/03)
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- The total synthesis of (+)-petasin and (+)-isopetasin
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Petasin 1 and isopetasin 2, anti-inflammatory and analgesic components of the butterbur (Petasites hybridus), were prepared for the first time in a short and enantioselective synthesis. The key steps were a Michael addition/alkylation (7 → 8), an enamine alkylation to give 9 and a cyclization with N-phenyliminoketenylidenetriphenylphosphorane 11 (10 → 15).
- Witschel, Matthias C.,Bestmann, Hans Jürgen
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p. 107 - 112
(2007/10/03)
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- Synthese der Pestwurzinhaltsstoffe (+)-Petasin und (+)-Isopetasin
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The first total synthesis of optically active petasine 1 and isopetasine 2 succeeded by applying an annelation reaction, based on the reaction of cyclic δ-ketocarboxylic acids with N-phenyliminoketenylidenetriphenylphosphorane. 1 and 2 are biologically ac
- Witschel, Matthias Christian,Bestmann, Hans Juergen
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p. 3325 - 3328
(2007/10/02)
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- Improved preparation of angelate esters
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A new procedure has been developed for the efficient preparation of angelate esters from alcohols. The alcohol is treated in dry toluene at 70-80°C for 19-36 h with a mixed anhydride prepared from angelic acid and 2,4,6-trichlorobenzoyl chloride. In the absence of base, no tiglate ester is produced.
- Hartmann, Benoit,Kanazawa, Alice M.,Depres, Jean-Pierre,Greene, Andrew E.
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p. 5077 - 5080
(2007/10/02)
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