Reaksi Achmatowicz

Reaksi Achmatowicz merupakan sebuah sintesis organik yang mana furan diubah menjadi dihidropiran. Pada publikasi awanya oleh Osman Achmatowicz Jr. pada tahun 1971^[1] furfuril alkohol direaksikan dengan bromin dalam metanol menjadi 2,5-dimetoksi-2,5-dihidrofuran yang akan ditata ulang menjadi dihidropiran dengan menggunakan asam sulfat encer. Langkah reaksi tambahan, perlindungan alkohol dengan metil ortoformat dan boron trifluorida serta reduksi keton dengan natrium borohidrida akan menghasilkan zat antara yang dapat digunakan untuk mensintesis beragam monosakarida.

Reaksi ini banyak digunakan dalam sintesis total, misalnya pada sintesis desoksoprosofilina,^[2] Pirenoforin^[3] dan Bao Gong Teng A.^[4] Baru-baru ini, ia telah digunakan dalam sintesis berorientasi keanekaragaman^[5]^{[n 1]}

dan pada perancahan enansiomer .^{[n 2]}^[6]

Catatan kaki

^ Pereaksi: NBS, PPTS, untuk macrobeads lihat: sintesis fasa padat
^ Pereaksi: benzil kloroformat melindungi amina sebagai gugus Cbz, reaksi Achmatowitz dengan m-CPBA, kompleksasi dengan suatu senyawa molibdenum, Cp adalah siklopentadienil

Referensi

^ O. Achmatowicz, P. Bukowski, B. Szechner, Z. Zwierzchowska and A. Zamojski (1971), "Synthesis of methyl 2,3-dideoxy--alk-2-enopyranosides from furan compounds : A general approach to the total synthesis of monosaccharides", Tetrahedron, 27 (10): 1973–1996, doi:10.1016/S0040-4020(01)98229-8
^ Cui-Fen Yang, Yi-Ming Xu, Li-Xin Liao and Wei-Shan Zhou (10 December 1998), "Asymmetric total synthesis of (+)-desoxoprosophylline", Tetrahedron Letters, 39 (50): 9227–9228, doi:10.1016/S0040-4039(98)02129-7
^ Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. (1998), Article, "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", J. Org. Chem., 63 (21): 7505–7515, doi:10.1021/jo980942a
^ Yongqiang Zhang and Lanny S. Liebeskind (2006), Article, "Organometallic Enantiomeric Scaffolding: Organometallic Chirons. Total Synthesis of (-)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition", J. Am. Chem. Soc., 128 (2): 465 – 472, doi:10.1021/ja055623x
^ Martin D. Burke, Eric M. Berger, and Stuart L. Schreiber J. (2004), "A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially", J. Am. Chem. Soc., 126 (43): 14095 –14104, doi:10.1021/ja0457415
^ Thomas C. Coombs, Maurice D. Lee, IV, Heilam Wong, Matthew Armstrong, Bo Cheng, Wenyong Chen, Alessandro F. Moretto, and Lanny S. Liebeskind (2008), "Practical, Scalable, High-Throughput Approaches to 3-Pyranyl and 3-Pyridinyl Organometallic Enantiomeric Scaffolds Using the Achmatowicz Reaction", J. Org. Chem., 73 (3): 882–888, doi:10.1021/jo702006z

[6] Pereaksi: NBS, PPTS, untuk macrobeads lihat: sintesis fasa padat

[7] Pereaksi: benzil kloroformat melindungi amina sebagai gugus Cbz, reaksi Achmatowitz dengan m-CPBA, kompleksasi dengan suatu senyawa molibdenum, Cp adalah siklopentadienil

[1] O. Achmatowicz, P. Bukowski, B. Szechner, Z. Zwierzchowska and A. Zamojski (1971), "Synthesis of methyl 2,3-dideoxy--alk-2-enopyranosides from furan compounds : A general approach to the total synthesis of monosaccharides", Tetrahedron, 27 (10): 1973–1996, doi:10.1016/S0040-4020(01)98229-8

[2] Cui-Fen Yang, Yi-Ming Xu, Li-Xin Liao and Wei-Shan Zhou (10 December 1998), "Asymmetric total synthesis of (+)-desoxoprosophylline", Tetrahedron Letters, 39 (50): 9227–9228, doi:10.1016/S0040-4039(98)02129-7

[3] Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. (1998), Article, "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", J. Org. Chem., 63 (21): 7505–7515, doi:10.1021/jo980942a

[4] Yongqiang Zhang and Lanny S. Liebeskind (2006), Article, "Organometallic Enantiomeric Scaffolding: Organometallic Chirons. Total Synthesis of (-)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition", J. Am. Chem. Soc., 128 (2): 465 – 472, doi:10.1021/ja055623x

[5] Martin D. Burke, Eric M. Berger, and Stuart L. Schreiber J. (2004), "A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially", J. Am. Chem. Soc., 126 (43): 14095 –14104, doi:10.1021/ja0457415

[8] Thomas C. Coombs, Maurice D. Lee, IV, Heilam Wong, Matthew Armstrong, Bo Cheng, Wenyong Chen, Alessandro F. Moretto, and Lanny S. Liebeskind (2008), "Practical, Scalable, High-Throughput Approaches to 3-Pyranyl and 3-Pyridinyl Organometallic Enantiomeric Scaffolds Using the Achmatowicz Reaction", J. Org. Chem., 73 (3): 882–888, doi:10.1021/jo702006z

[1]

[2]

[3]

[4]

[5]

[n 1]

[n 2]

[6]

Reaksi Achmatowicz

Catatan kaki

Referensi

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