Stereoselective Allylation of Linear and Chiral β-Amino-α-Hydroxy Aldehydes: Total Syntheses of Tetraacetyl d-lyxo-, d-ribo-, and d-arabino-Phytosphingosines

Abstract

The stereoselective allylations of β-amino-α-hydroxy aldehydes­ are described. Several Lewis acids (BF₃·OEt₂, SnCl₄, TiCl₄, ZnCl_2­, and MgBr₂·OEt₂) were utilized in the allylations. The allylation of anti-β-NHCbz-α-OTBS substrate mediated by SnCl₄ afforded the syn-selective­ product, while its allylation mediated by BF₃·OEt₂ afforded the anti-selective product. The allylation of syn-β-NHCbz-α-OTBS mediated by SnCl₄ afforded the anti-selective product. The mechanism involves the chelation between the amido group and aldehyde oxygen by SnCl₄, and the Felkin–Anh model by BF₃·OEt₂. The resulting allylation products were used for the total syntheses of tetraacetyl d-lyxo-, d-ribo-, and d-arabino-phytosphingosines.

• References

• 1a Jurczak J. Golebiowski A. Chem. Rev. 1989; 89: 149
• 1b Reetz MT. Angew. Chem., Int. Ed. Engl. 1991; 30: 1531
• 1c Marshall JA. Chem. Rev. 1996; 96: 31
• 1d Bergmeier SC. Tetrahedron 2000; 56: 2561
• 1e Liang X. Andersch J. Bols M. J. Chem. Soc., Perkin Trans. 1 2001; 2136
• 1f Hili R. Baktharaman S. Yudin AK. Eur. J. Org. Chem. 2008; 5201
• 1g Karjalainen OK. Koskinen AM. Org. Biomol. Chem. 2012; 10: 4311
• 1h Passiniemi M. Koskinen AM. Beilstein J. Org. Chem. 2013; 9: 2641
• 2 Cram DJ. Elhafez FA. A. J. Am. Chem. Soc. 1952; 74: 5828
• 3a Mengel A. Reiser O. Chem. Rev. 1999; 99: 1191
• 3b Reetz MT. Angew. Chem., Int. Ed. Engl. 1984; 23: 556
• 3c Reetz MT. Acc. Chem. Res. 1993; 26: 462
• 3d Yamamoto Y. Asao N. Chem. Rev. 1993; 93: 2207
• 3e Yus M. González-Gómez JC. Foubelo F. Chem. Rev. 2013; 113: 5595
• 4 Gung BW. Org. React. 2004; 64: 1
• 5 Dondoni A. Fantin G. Fogagnolo M. Medici A. J. Chem. Soc., Chem. Commun. 1988; 10
• 6 Shimizu M. Wakioka I. Fujisawa T. Tetrahedron Lett. 1997; 38: 6027
• 7 Ndakala AJ. Hashemzadeh M. So RC. Howell AR. Org. Lett. 2002; 4: 1719
• 8 Wagner A. Mollath M. Tetrahedron Lett. 1993; 34: 619
• 9a Ghosh AK. Bischoff A. Cappiello J. Org. Lett. 2001; 3: 2677
• 9b Ghosh AK. Bischoff A. Cappiello J. Eur. J. Org. Chem. 2003; 821
• 10 Ginesta X. Pastó M. Pericas MA. Riera A. Org. Lett. 2003; 5: 3001
• 11 Righi G. Ciambrone S. D’Achille C. Leonelli A. Bonini C. Tetrahedron 2006; 62: 11821
• 12 Abraham E. Candela-Lena JI. Davies SG. Georgiou M. Nicholson RL. Roberts PM. Russell AJ. Sánchez-Fernández EM. Smith AD. Thomson JE. Tetrahedron: Asymmetry 2007; 18: 2510
• 13a Murakami T. Taguchi K. Tetrahedron 1999; 55: 989
• 13b Abraham E. Brock EA. Candela-Lena JI. Davies SG. Georgiou M. Nicholson RL. Perkins JH. Roberts PM. Russell AJ. Sánchez-Fernández EM. Org. Biomol. Chem. 2008; 6: 1665
• 14a Génisson Y. Lamandé L. Salma Y. Andrieu-Abadie N. André C. Baltas M. Tetrahedron: Asymmetry 2007; 18: 857
• 14b Salma Y. Ballereau S. Maaliki C. Ladeira S. Andrieu-Abadie N. Génisson Y. Org. Biomol. Chem. 2010; 8: 3227
• 15a Singh S. Han H. Tetrahedron Lett. 2004; 45: 6349
• 15b Singh OV. Kampf DJ. Han H. Tetrahedron Lett. 2004; 45: 7239
• 15c Chikkanna D. Singh OV. Kong SB. Han H. Tetrahedron Lett. 2005; 46: 8865
• 16 Busscher GF. Rutjes FP. van Delft FL. Tetrahedron Lett. 2004; 45: 3629
• 17a Lee K.-Y. Kim Y.-H. Park M.-S. Oh C.-Y. Ham W.-H. J. Org. Chem. 1999; 64: 9450
• 17b Jin T. Mu Y. Kim J.-S. Park S.-H. Jin X. Kang J.-C. Oh C.-Y. Ham W.-H. Synth. Commun. 2014; 44: 2401
• 17c Myeong I.-S. Lee Y.-T. Lee S.-H. Jung C. Kim J.-S. Park S.-H. Kang J. Lee S.-J. Ye I.-H. Ham W.-H. Tetrahedron: Asymmetry 2017; 28: 1053
• 18a Li Y.-L. Mao X.-H. Wu Y.-L. J. Chem. Soc., Perkin Trans. 1 1995; 1559
• 18b Shirota O. Nakanishi K. Berova N. Tetrahedron 1999; 55: 13643
• 18c Nakamura T. Shiozaki M. Tetrahedron Lett. 1999; 40: 9063
• 18d Fernandes RA. Kumar P. Tetrahedron Lett. 2000; 41: 10309
• 18e Nakamura T. Shiozaki M. Tetrahedron 2001; 57: 9087
• 18f Lu X. Byun H.-S. Bittman R. J. Org. Chem. 2004; 69: 5433
• 18g Cai Y. Ling C.-C. Bundle DR. Org. Biomol. Chem. 2006; 4: 1140
• 18h Park J.-J. Lee JH. Li Q. Diaz K. Chang Y.-T. Chung S.-K. Bioorg. Chem. 2008; 36: 220
• 18i Mu Y. Kim J.-Y. Jin X. Park S.-H. Joo J.-E. Ham W.-H. Synthesis 2012; 44: 2340
• 18j Mridha M. Ma G. Palo-Nieto C. Afewerki S. Cordova A. Synthesis 2017; 49: 383
• 19a He L. Byun H.-S. Bittman R. J. Org. Chem. 2000; 65: 7618
• 19b Chiu H.-Y. Tzou D.-LM. Patkar LN. Lin C.-C. J. Org. Chem. 2003; 68: 5788
• 19c Lombardo M. Capdevila MG. Pasi F. Trombini C. Org. Lett. 2006; 8: 3303
• 19d Llaveria J. Díaz Y. Matheu MI. Castillón S. Org. Lett. 2008; 11: 205
• 19e Liu Z. Byun H.-S. Bittman R. J. Org. Chem. 2010; 75: 4356
• 19f Lee YM. Baek DJ. Lee S. Kim D. Kim S. J. Org. Chem. 2010; 76: 408
• 19g Perali RS. Mandava S. Chalapala S. Tetrahedron 2011; 67: 9283
• 19h Devi TJ. Saikia B. Barua NC. Tetrahedron 2013; 69: 3817
• 19i Yen Y.-F. Sawant R. Luo S.-Y. Synthesis 2013; 45: 511
• 19j Calder ED. Zaed AM. Sutherland A. J. Org. Chem. 2013; 78: 7223
• 19k Chun JS. Hong SM. Jeon TH. Park SJ. Son HP. Jung JM. Choi YJ. Kim IS. Jung YH. Tetrahedron 2016; 72: 8550
• 20a Azuma H. Tamagaki S. Ogino K. J. Org. Chem. 2000; 65: 3538
• 20b Enders D. Paleček J. Grondal C. Chem. Commun. 2006; 655
• 20c Mormeneo D. Casas J. Llebaria A. Delgado A. Org. Biomol. Chem. 2007; 5: 3769
• 20d Kim S. Lee N. Lee S. Lee T. Lee YM. J. Org. Chem. 2008; 73: 1379
• 20e Mu Y. Jin T. Kim GW. Kim JS. Kim SS. Tian YS. Oh CY. Ham WH. Eur. J. Org. Chem. 2012; 2614
• 20f Haghshenas P. Gravel M. Org. Lett. 2016; 18: 4518
• 21a Riethmüller J. Riehle A. Grassmé H. Gulbins E. Biochim. Biophys. Acta 2006; 1758: 2139
• 21b Snook C. Jones J. Hannun Y. Biochim. Biophys. Acta 2006; 1761: 927
• 22 Zhou S. Zhou H. Walian PJ. Jap BK. Biochemistry 2007; 46: 2553
• 23 Summers SA. Nelson DH. Diabetes 2005; 54: 591
• 24 Modrak DE. Gold DV. Goldenberg DM. Mol. Cancer Ther. 2006; 5: 200