Achmatowicz reaction

Achmatowicz Reaction jẹ́ ìṣètò organic èyí tí furan ma a ń yípadà sí dihydropyran. Ní àtẹ̀jáde Osman Achmatowicz Jr. àkọ́kọ́ ní ọdún 1971 ^[1] furfuryl alcohol dàpapọ̀ ṣiṣẹ́ pẹ̀lú bromine ní methanol sí 2,5-dimethoxy-2,5-dihydrofuran tí ó tún ara ṣàjọ sí dihydropyran pẹ̀lú àdàpọ̀ sulfuric acid. Àwọn ìgbésẹ̀ ìdàpapọ̀ ṣiṣẹ́ míràn, ìdáàbòbò alcohol pẹ̀lú methyl orthoformate àti boron trifluoride) àti ìmúkù ketone pẹ̀lú sodium borohydride ṣe ìmújáde èyí tí a lè ṣètò monosaccharides lati inú rẹ̀.

Wọ́n ti lo ìlànà Achmatowitz lati ṣètò àwọn molecule tó lágbára fún àpẹẹrẹ bí tidesoxoprosophylline,^[2] Pyrenophorin ^[3] àti Bao Gong Teng A.^[4] Láìpẹ́ yìí wọ́n lòó fún ìmú ìlọsíwájú bá ìṣètò kẹ́míkà.^[5]^[6]

àti ní enantiomeric scaffolding.^[7]^[8]

Àwọn ìtọ́kasí

↑ 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
↑ 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
↑ 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.
↑ Organometallic Enantiomeric Scaffolding: Organometallic Chirons.
↑ A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially Martin D. Burke, Eric M. Berger, and Stuart L. Schreiber J. Am. Chem.
↑ Reagents: NBS, PPTS, for macrobeads see: solid-phase synthesis
↑ 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.
↑ Reagents: benzyl chloroformate protects amine as Cbz group, Achmatowitz reaction with m-CPBA, complexation with a molybdenum compound, Cp is cyclopentadienyl

[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.

[4] Organometallic Enantiomeric Scaffolding: Organometallic Chirons.

[5] A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially Martin D. Burke, Eric M. Berger, and Stuart L. Schreiber J. Am. Chem.

[6] Reagents: NBS, PPTS, for macrobeads see: solid-phase synthesis

[7] 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.

[8] Reagents: benzyl chloroformate protects amine as Cbz group, Achmatowitz reaction with m-CPBA, complexation with a molybdenum compound, Cp is cyclopentadienyl

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