137601-32-2Relevant articles and documents
Studies on the stereostructure of eudesmanolides from Umbelliferae: Total synthesis of (+)-decipienin A
Macías, Francisco A.,Aguilar, José María,Molinillo, José María G.,Rodríguez-Luís, Francisco,Collado, Isidro G.,Massanet, Guillermo M.,Fronczek, Frank R.
, p. 3409 - 3414 (2000)
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
Asymmetric synthesis of 3β-angeloyloxy-4β-hydroxyeudesman-8-one, purported sesquiterpene from pluchea quitoc
Muri, Estela,Kanazawa, Alice,Barreiro, Eliezer,Greene, Andrew E.
, p. 731 - 735 (2000)
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
Enantioselective synthesis of (+)-decipienin A
Aladro, F.Javier,Guerra, Francisco M,Moreno-Dorado, F.Javier,Bustamante, Jesús M,Jorge, Zacarías D,Massanet, Guillermo M
, p. 2171 - 2178 (2001)
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
Synthesis of mono- and sesquiterpenoids; XXIV: (-)-Homogynolide A, an insect antifeedant isolated from Homogyne alpina
Mori,Matsushima
, p. 845 - 850 (1995)
(-)-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
Semisynthesis of (+)-angeloyl-gutierrezianolic acid methyl ester diterpenoid
Marcos,Benéitez,Moro,Basabe,Díez,Urones
, p. 8605 - 8614 (2010)
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
A METHOD OF PRODUCING INGENOL-3-ANGELATE
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Page/Page column 36, (2012/02/05)
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.
Semisynthesis of ingenol 3-angelate (PEP005): Efficient stereoconservative angeloylation of alcohols
Liang, Xifu,Grue-Sorensen, Gunnar,Petersen, Anders Klarskov,H?gberg, Thomas
supporting information, p. 2647 - 2652 (2013/01/15)
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
Asymmetrie total syntheses of (-)-renieramycin M and G and (-)-jorumycin using aziridine as a lynchpin
Wu, Yan-Chao,Zhu, Jieping
supporting information; experimental part, p. 5558 - 5561 (2010/02/28)
"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.
Synthesis and cytotoxic evaluation of some cribrostatin-ecteinascidin analogues
Wright, Benjamin J. D.,Chan, Collin,Danishefsky, Samuel J.
experimental part, p. 409 - 414 (2009/04/05)
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.
Total synthesis of thapsigargin, a potent SERCA pump inhibitor
Ball, Matthew,Andrews, Stephen P.,Wierschem, Frank,Cleator, Ed,Smith, Martin D.,Ley, Steven V.
, p. 663 - 666 (2008/02/05)
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).