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Achmatowicz reaction

Lianyungang Klinechem Co.,Ltd | Updated: Nov 28, 2018

The Achmatowitz protocol has been used in total synthesis, including those of desoxoprosophylline,[2] pyrenophorin [3][4] Very recently it has been used in diversity oriented synthesis [5][6]

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and in enantiomeric scaffolding.[7][8]

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References

1.   Jump up^ 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

2.   Jump up^ 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

3.   Jump up^ 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

4.     Jump up^ 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

5.   Jump up^ 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

6.   Jump up^ Reagents: NBSPPTS, for macrobeads see: solid-phase synthesis

7.   Jump up^ 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

8.   Jump up^ Reagents: benzyl chloroformate protects amine as Cbz group, Achmatowitz reaction with m-CPBA, complexation with a molybdenum compound, Cp is cyclopentadienyl anion

 


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