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Achmatowicz Reaction

Osman Achmatowicz Jr. (yyyy–yyyy). .

In 1971, Osman Achmatowicz Jr. reported preparation of dihydropyran.1) furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute sulfuric acid. This reaction has been extended to produce monosccharide. Alcohol protection with methyl orthoformate and boron trifluoride) and ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.

Main Features

  • A furan is converted to a dihydropyran.
  • Also known as .
  • Byproduct:
  • Drawbacks :
  • Driving force:

Reaction Mechanism

Synthetic Application

Total synthesis of desoxoprosophylline,2) Pyrenophorin 3) and Bao Gong Teng A.4)

Similar Reactions Achmatowicz Reaction

1) 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) 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) 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) 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
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named/reactions/achmatowicz_reaction.txt · Last modified: 2014/12/08 21:29 (external edit)

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