148441-26-3Relevant academic research and scientific papers
Silver-promoted Friedel-Crafts reaction: Concise total synthesis of (-)-ardeemin, (-)-acetylardeemin and (-)-formylardeemin
Wang,Kong,Du,Song,Zhang,Qin
supporting information, p. 2793 - 2797 (2012/11/13)
Total syntheses of multidrug resistant inhibitors (-)-acetylardeemin 2a, (-)-ardeemin 2b, and (-)-formylardeemin 3 have been achieved within 10 steps starting from bromopyrroloinoline 13. The key step involves direct alkylation of 13 with prenyl tributylstannane 11 to yield 12via a silver-promoted asymmetric Friedel-Crafts reaction. Highly efficient installation of the isoprenyl group allowed excellent overall yield. Moreover, the substrate scope of the asymmetric Friedel-Crafts reaction of 13 was expanded to include a variety of arenes 14 to afford natural product-like library analogues 15. The Royal Society of Chemistry 2012.
Total syntheses of (-)-fructigenine A and (-)-5-N-acetylardeemin
Takiguchi, Satoshi,Iizuka, Toshimasa,Kumakura, Yuh-Suke,Murasaki, Kohta,Ban, Naoko,Higuchi, Kazuhiro,Kawasaki, Tomomi
experimental part, p. 1126 - 1131 (2010/04/04)
(Chemical Equation Presented) The first total synthesis of (-)-fructigenine A and a novel approach to (-)-5-N-acetylardeemin through a common imine intermediate (+)-3 are described. The key steps include highly enantioselective preparation of (+)-3 via domino olefination/isomerization/Claisen rearrangement (OIC) of 5, reductive cyclization (RC), and regioselective oxidation of (-)-4 and a novel assembly of the pyrazino ring of these alkaloids via Ugi three-component reaction/cyclization of (+)-3 with the corresponding amino acid and isonitrile.
Total synthesis of (-)-ardeemin
He, Bin,Song, Hao,Du, Yu,Qin, Yong
experimental part, p. 298 - 304 (2009/04/07)
(Chemical Equation Presented) Total synthesis of potent anti-MDR indole alkaloids (-)-ardeemin and its N-acyl analogues has been accomplished from L-tryptophan with about 2% overall yield in 20 steps. The key step depended on the newly developed three-ste
ANALOGUES OF N-ACETYLARDEEMIN, METHOD OF PREPARATION AND USES THEREOF
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Page/Page column 21, (2010/11/28)
The present invention provides a compound having the structure: wherein R1 R6 and R7 are independently hydrogen, OH, NH2, SH, halogen, C1-C9 linear or branched chain alkyl, alkylmercapto, alkylamino, dialkylamino, alkoxy, phenyl, etc.; wherein R0 and R2 are independently hydrogen, OH, linear or branched chain alkyl, -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4; wherein R3 and R4 are independently hydrogen, halogen, C1-C9 linear or branched chain alkyl, phenyl, etc.; wherein R5 is hydrogen, C1-C9 linear or branched chain alkyl, phenyl, etc.; and wherein R8 is hydrogen, C1-C9 linear or branched chain acyl, benzoyl, etc.; with the proviso that (a) when R2 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R2 is hydrogen; (b) when R0 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R2 is OH; and (c) when (i) R0 or R2 is -CR3R3-CH=CHR4, (ii) R3 and R5 are CH3 and (iii) R4 is hydrogen, then R1, R6 and R7 are not all hydrogen. Also provided are related compounds and compositions, and methods of inhibiting the growth of multidrug resistant cells by means of MDR reversal, collateral sensitivity and quantitative synergism.
Total synthesis of 5-N-acetylardeemin and amauromine: Practical routes to potential MDR reversal agents
Depew, Kristopher M.,Marsden, Stephen P.,Zatorska, Danuta,Zatorski, Andrzej,Bornmann, William G.,Danishefsky, Samuel J.
, p. 11953 - 11963 (2007/10/03)
The total synthesis of the title compounds has been accomplished. The key step involves the kinetic stereoselective conversion of 19 → 20. The synthesis of 20 represents for the first time a direct method for constructing exo-pyrroloindoles from protected
