Synthesis, Inhaltsverzeichnis Synthesis 2022; 54(12): 2849-2855DOI: 10.1055/a-1768-2082 paper Concise Synthesis of (S)-7-Hydroxy-5-aza-8a-epi-d-swainsonine from a d-Erythrose Derivative Authors Cristina E. A. Sousa ∗ Daniela A. L. Salgueiro Maria J. Alves Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract A five-step synthesis of (S)-7-hydroxy-5-aza-8a-epi-d-swainsonine [(3S,4S,4aS,5S,6R)-octahydropyrrolo[1,2-b]pyridazine-3,4,5,6-tetraol] was accessed in good overall yield from readily available d-erythrosyl benzylidene acetal buta-1,3-diene. The key step of the reaction sequence is a full stereoselective Diels–Alder cycloaddition between the diene and dienophile: diethyl azodicarboxylate (DEAD) or di-tert-butyl azodicarboxylate (DBAD). The cycloadducts were further transformed into the title 5-aza-indolizidine. Optimized procedures were obtained for the synthesis of intermediates and products. Key words Key wordsiminosugar - Diels–Alder - 5-aza-indolizidine - swainsonine - pyrrolo[1,2-b]pyridazine Volltext Referenzen References 1a Compain P, Martin OR. Iminosugars: From Synthesis to Therapeutic Applications . Wiley; Chichester: 2007 1b Horne G, Wilson FX, Tinsley J, Williams DH, Storer R. Drug Discovery Today 2011; 16: 107 1c Racine E, Bello C, Gerber-Lemaire S, Vogel P, Py S. J. Org. Chem. 2009; 74: 1766 1d Cruz AV. D, Kanazawa A, Poisson J.-F, Behr J.-B, Py S. J. Org. Chem. 2017; 82: 9866 1e Gilles P, Py S. Org. Lett. 2012; 14: 1042 1f Kaliappan KP, Das P, Chavan ST, Sabharwal SG. J. Org. Chem. 2009; 74: 6266 1g Kaliappan KP, Das P. Synlett 2008; 841 2a Winchester B, Aldaher S, Carpenter NC, Dibello IC, Choi SS, Fairbanks AJ, Fleet GW. J. Biochem. J. 1993; 290: 743 2b Cenci Di Bello I, Fleet GW. J, Namgoong SK, Tadano K, Winchester B. Biochem. J. 1989; 259: 855 3a van den Elsen JM. H, Kuntz DA, Rose DR. EMBO J. 2001; 20: 3008 3b Rose DR. Curr. Opin. Struct. Biol. 2012; 22: 558 4a Nash RJ, Kato A, Yu CY, Fleet GW. J. Future Med. Chem. 2011; 3: 1513 4b Brás NF, Cerqueira NM, Ramos MJ, Fernandes PA. Expert Opin. Ther. Pat. 2014; 24: 857 5 Asano N, Kuroi H, Ikeda K, Kizu H, Kameda Y, Kato A, Adachi I, Watson AA, Nash RJ, Fleet GW. J. Tetrahedron: Asymmetry 2000; 11: 1645 6 Moremen KW. Biochim. Biophys. Acta 2002; 1573: 225 7a Fujita T, Nagasawa H, Uto Y, Hashimoto T, Asakawa Y, Hori H. Org. Lett. 2004; 6: 827 7b Kuntz DA, Nakayama S, Shea K, Hori H, Uto Y, Nagasawa H, Rose DR. ChemBioChem 2010; 11: 673 8 Bols M, Hazell RG, Thomsen IbB. Chem. Eur. J. 1997; 3: 940 9 Alves MJ, Duarte VC. M, Faustino H, Fortes AG. Tetrahedron: Asymmetry 2010; 21: 1817 10 Duarte VC. M, Faustino H, Alves MJ, Gil Fortes A, Micaelo N. Tetrahedron: Asymmetry 2013; 24: 1063 11 Salgueiro DA. L, Duarte VC. M, Sousa CE. A, Alves MJ, Gil Fortes A. Synlett 2012; 23: 1765 12a Baker SR, Mckillop C. Tetrahedron Lett. 1988; 29: 991 12b Zimmermann P, Schimdt RR. Liebigs Ann. Chem. 1988; 663 12c Freitas DS, Sousa CE. A, Parente J, Drogalin A, Gil Fortes A, Cerqueira NM. F. S. A, Alves MJ. Org. Biomol. Chem. 2019; 17: 10052 Zusatzmaterial Zusatzmaterial Supporting Information (PDF)
