Achmatowicz reaction

Achmatowicz reaction

The Achmatowicz Reaction is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by Osman Achmatowicz Jr. in 1971 ["Synthesis of methyl 2,3-dideoxy--alk-2-enopyranosides from furan compounds : A general approach to the total synthesis of monosaccharides" Tetrahedron, Volume 27, Issue 10, 1971, Pages 1973-1996 O. Achmatowicz, P. Bukowski, B. Szechner, Z. Zwierzchowska and A. Zamojski DOI|10.1016/S0040-4020(01)98229-8] furfuryl alcohol is reacted with bromine in methanol to "2,5-dimethoxy-2,5-dihydrofuran" which rearranges to the dihydropyran with dilute sulfuric acid. Additional reaction steps, alcohol protection with methyl orthoformate and boron trifluoride) and ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.

:

The Achmatowitz protocol has been used in total synthesis for example that of "desoxoprosophylline" ["Asymmetric total synthesis of (+)-desoxoprosophylline" Tetrahedron Letters, Volume 39, Issue 50, 10 December 1998, Pages 9227-9228 Cui-Fen Yang, Yi-Ming Xu, Li-Xin Liao and Wei-Shan Zhou DOI|10.1016/S0040-4039(98)02129-7 ] , "Pyrenophorin" ["Efficient Conditions for Conversion of 2-Substituted Furans into 4-Oxygenated 2-Enoic Acids and Its Application to Synthesis of (+)-Aspicilin, (+)-Patulolide A, and (-)-Pyrenophorin" Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem.; (Article); 1998; 63(21); 7505-7515. DOI|10.1021/jo980942a ] and "Bao Gong Teng A" ["Organometallic Enantiomeric Scaffolding: Organometallic Chirons. Total Synthesis of (-)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition"Yongqiang Zhang and Lanny S. Liebeskind J. Am. Chem. Soc. 2006; 128(2) pp 465 - 472; (Article) DOI|10.1021/ja055623x] . Very recently it has been used in diversity oriented synthesis ["A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially" Martin D. Burke, Eric M. Berger, and Stuart L. Schreiber J. Am. Chem. Soc. 126 (43), 14095 -14104, 2004. DOI|10.1021/ja0457415 ] [Reagents: NBS, PPTS, for macrobeads see: solid-phase synthesis]

:

and in enantiomeric scaffolding ["Practical, Scalable, High-Throughput Approaches to 3-Pyranyl and 3-Pyridinyl Organometallic Enantiomeric Scaffolds Using the Achmatowicz Reaction" Thomas C. Coombs, Maurice D. Lee, IV, Heilam Wong, Matthew Armstrong, Bo Cheng, Wenyong Chen, Alessandro F. Moretto, and Lanny S. Liebeskind J. Org. Chem. 73 (3), 882 -888, 2008. DOI|10.1021/jo702006z] [Reagents: benzyl chloroformate protects amine as Cbz group, Achmatowitz reaction with m-CPBA, complexation with a molybdenum compound, Cp is cyclopentadienyl] .

:

References


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать курсовую

Look at other dictionaries:

  • Osman Achmatowicz — (born April 16, 1899 in Bergaliszki – December 4, 1988 in Warsaw) was a Polish chemist of Lipka Tatar descent. His son, Osman Achmatowicz Jr., (also a chemist) is credited with the Achmatowicz reaction in 1971 …   Wikipedia

  • List of organic reactions — Well known reactions and reagents in organic chemistry include Contents: A B C D E F G H I J K L M N O P Q R S T U V W X Y Z    See also   Ext …   Wikipedia

  • Furan — This article is about the chemical industrial compound. For the unintentional contaminant byproduct, see Polychlorinated dibenzofurans. For other uses, see Furan (disambiguation). Furan …   Wikipedia

  • Chiral pool synthesis — is a strategy that aims to improve the efficiency of chiral synthesis. It starts the organic synthesis of a complex enantiopure chemical compound from a stock of readily available enantiopure substances. Common chiral starting materials include… …   Wikipedia

  • Anexo:Reacciones orgánicas — A continuación se presentan las reacciones orgánicas, reactivos, métodos de síntesis y pruebas de ensayo más comunes en Química Orgánica.[1] [2] [3] Contenido …   Wikipedia Español

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”