- A new total synthesis of (±)-α-noscapine
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A new, convergent total synthesis of (±)-α-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.
- Mao, Yongjun,Song, Shuai,Zhao, Dongmei,Cheng, Maosheng
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p. 2633 - 2640
(2014/01/06)
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- Unnatural C-1 homologues of pancratistatin-Synthesis and promising biological activities
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Several C-1 homologues of pancratistatin and 7-deoxypancratistatin were synthesized by a phenanthrene-phenathridone oxidative recyclization strategy. The key steps involved the enzymatic dihydroxylation of bromobenzene, addition of an aryl alane to an epo
- Vshyvenko, Sergey,Scattolon, Jon,Hudlicky, Tomas,Romero, Anntherese E.,Kornienko, Alexander,Ma, Dennis,Tuffley, Ian,Pandey, Siyaram
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p. 932 - 943
(2013/02/22)
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- Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation
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The synthesis of two C-1 analogues of pancratistatin has been accomplished in 17 steps from bromobenzene. The key steps involved the enzymatic dihydroxylation, regioselective opening of epoxyaziridine 9 with the alane derived from 8, a solid-state silica-
- Vshyvenko, Sergey,Scattolon, Jon,Hudlicky, Tomas,Romero, Anntherese E.,Kornienko, Alexander
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scheme or table
p. 4750 - 4752
(2011/09/16)
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- First total synthesis of (±)-powelline
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The first total synthesis of (±)-powelline is reported in 10% overall yield over eight steps using an intramolecular oxidative phenolic coupling reaction as the key reaction.
- Anwar, Hany F.,Hansen, Trond Vidar
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scheme or table
p. 2681 - 2683
(2009/04/21)
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- A convenient synthesis of 4-alkoxylated isoindolin-1-ones
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A short synthesis of 4-alkoxylated isoindolin-1-ones based upon the S NAr reaction applied to phosphorylated 2-methoxybenzamides followed by alkaline cleavage of the phosphoryl auxiliary is reported.
- Moreau, Anne,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
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p. 1664 - 1670
(2007/10/03)
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- THE SYNTHESIS OF 6-METHOXY-7,8-METHYLENEDIOXYISOQUINOLINE DERIVATIVES
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Several new 6-methoxy-7,8-methylenedioxyisoquinolines were synthesized starting from 4-methoxy-2,3-methylenedioxybenzaldehyde.
- Simig, Gy.,Schlosser, M.
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p. 217 - 228
(2007/10/02)
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- PREPARATION OF 2-METHOXY-3,4-METHYLENEDIOXYBENZALDEHYDE (CROWEACIN ALDEHYDE) FROM PYROGALLOL
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2-Methoxy-3,4-methylenedioxybenzaldehyde (croweacin aldehyde) of high purity was prepared in 55percent overall yield from pyrogallol.
- Shirasaka, Tadashi,Takuma, Yuki,Imaki, Naoshi
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p. 1213 - 1221
(2007/10/02)
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- Synthesis of Cotarnin Iodide
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Starting from 4-methoxy-1,3-benzodioxol-5-carbaldehyde (croweacin aldehyde, 3) a six-step synthesis of cotarnin iodide (9, 67percent total yield) is described. - Keywords.Croweacinaldehyde; Isoquinoline; Cotarnin iodide.
- Fleischhacker, Wilhelm,Richter, Bernd,Urban, Ernst
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p. 765 - 770
(2007/10/02)
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- The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 21. A Mild Process For The Preparation of 10-Alkyl-9-acridanones And It's Application To The Synthesis of Acridone Alkaloids
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10-Substituted-9-acridanones are readily prepared by the reaction of the corresponding isatoic anhydride with the lithium enolate of 2-cyclohexen-1-one.The initially formed product, the 1,2-dihydroacridone need not be purified but can be aromatized directly with DDQ to the desired acridone.This methodology is applicable to the synthesis of acridone natural products.Two alkaloids, 1,2,3-trimethoxy-10-methylacridone (9) and evoxanthine (10), were prepared from 4,5,6-trimethoxy-N-methylisatoic anhydride and 6-methoxy-4,5-methylenedioxy-N-methylisatoic anhydride respectively.In these trioxygenated systems, palladium-on-charcoal must be used to aromatize the penultimate intermediate.
- Coppola, Gary M.,Schuster, Herbert F.
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p. 957 - 964
(2007/10/02)
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- Synthesis of the Yeast Antioxidant Benzofuran and Analogues
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2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran, the active antioxidant which occurs in yeasts, and related 2-arylbenzofurans have been synthesized by a convergent route.The key step involves benzofuran formation by an intramolecular Wittig reaction.
- McKittrick, Brian A.,Stevenson, Robert
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p. 709 - 712
(2007/10/02)
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- SYNTHESE TOTALES DE LA (+/-) ISO β-PELTATINE ET DE SES ANALOGUES
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α-Hydroxyalkylation of a β-(2-alkoxy 3,4-methylenedioxy benzyl)-γ-butyrolactone (17 or 25) with 3,4,5-trimethoxybenzaldehyde or syringaldehyde 27, followed by cyclisation, afforded good yields of the corresponding (+/-) isopeltatins.
- Brown, Eric,Loriot, Michel,Robin, Jean-Pierre
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p. 949 - 952
(2007/10/02)
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- Astraciceran: a new isoflavan phytoalexin from Astragalus cicer
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A new phytoalexin isolated from the fungus-inoculated leaflets of Astragalus cicer has been identified as 7-hydroxy-2′-methoxy-4′,5′-methylenedioxyisoflavan (astraciceran). The synthesis of astraciceran and its 3′,4′-methylenedioxy analogue is described.
- Ingham, John L.,Dewick, Paul M.
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p. 1767 - 1770
(2007/10/02)
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