Total Synthesis of d-lyxo-Phytosphingosine and Formal Synthesis of Pachastrissamine via a Chiral 1,3-Oxazine

Abstract

Concise and efficient syntheses of d-lyxo-phytosphingosine and pachastrissamine were achieved utilizing a chiral oxazine. The key features in these strategies are the stereoselective intramolecular oxazine formation catalyzed by palladium(0), and intermolecular olefin cross-metathesis.

Key words

palladium catalysis - sphingolipids - stereoselective synthesis - cross-coupling - natural products

• References

• 1a Merrill AH. Jr, Sandhoff K. Sphingolipid Metabolism and Cell Signaling, In Biochemistry of Lipids, Lipoproteins, and Membranes . Vance DE, Vance JE. Elsevier; New York: 2002. 373
• 1b Merrill AH. Jr, Sweeley CC. In Biochemistry of Lipids, Lipoproteins, and Membranes . Vance DE, Vance JE. Elsevier; Amsterdam: 1996. 309
• 2a Morita M, Motoki K, Akimoto K, Natori T, Sakai T, Sawa E, Yamaji K, Koezuka Y, Kobayashi E, Fukushima H. J. Med. Chem. 1995; 38: 2176
• 2b Kobayashi E, Motoki K, Uchida T, Fukushima H, Koezuka Y. Oncol. Res. 1995; 7: 529
• 2c Kawano T, Cui J, Koezuka Y, Toura I, Kaneko Y, Motoki K, Ueno H, Nakagawa R, Sato H, Kondo E, Koseki H, Taniguchi M. Science 1997; 278: 1626
• 2d Miyamoto K, Miyake S, Yamamura T. Nature 2001; 413: 531
• 3a Kobayashi E, Motoki K, Yamaguchi Y, Uchida T, Fukushima H, Koezuka Y. Bioorg. Med. Chem. 1996; 4: 615
• 3b Zanolari B, Friant S, Funato K, Sutterlin C, Stevenson BJ, Riezman H. EMBO J. 2000; 19: 2824

For recent reviews of phytosphingosines, see:
• 4a Morales-Serna JA, Llaveria J, Diaz Y, Matheu MI, Castillón S. Curr. Org. Chem. 2010; 14: 2483
• 4b Liao J, Tao J, Lin D. Tetrahedron 2005; 61: 4715
• 4c Howell AR, Ndakala AJ. Curr. Org. Chem. 2002; 6: 365

For more recent syntheses of phytosphingosines, see:
• 5a Perali RS, Mandava S, Chalapala S. Tetrahedron 2011; 67: 9283
• 5b Rao GS, Rao BV. Tetrahedron Lett. 2011; 52: 4861
• 5c Martinkova M, Gonda J, Pomikalova K, Kozisek J, Kuchar J. Carbohydr. Res. 2011; 346: 1728
• 5d Ballereau S, Abadie NA, Saffon N, Génisson Y. Tetrahedron 2011; 67: 2570
• 5e Liu Z, Byun HS, Bittman R. J. Org. Chem. 2010; 75: 4356
• 5f Raghavan S, Krishnaiah V. J. Org. Chem. 2010; 75: 748
• 5g Dubey A, Kumar P. Tetrahedron Lett. 2009; 50: 3425
• 5h Pandey G, Tiwari DK. Tetrahedron Lett. 2009; 50: 3296

For recent syntheses of d -lyxo-phytosphingosine, see:
• 6a Rao GS, Rao BV. Tetrahedron Lett. 2011; 52: 6076
• 6b Lee YM, Baek DJ, Kim SW, Kim DJ, Kim SH. J. Org. Chem. 2011; 76: 408
• 6c Abraham E, Brock EA, Candela-Lena JI, Davies SG, Georgiou M, Nicholson RL, Perkins JH, Roberts PM, Russell AJ, Sanchez-Fernandez EM, Scott PM, Smith AD, Thomson JE. Org. Biomol. Chem. 2008; 6: 4668
• 6d Kim S, Lee N, Lee S, Lee T, Lee YM. J. Org. Chem. 2008; 73: 1379
• 7 Kuroda I, Musman M, Ohtani II, Ichiba T, Tanaka J, Garcia Gravalos D, Higa T. J. Nat. Prod. 2002; 65: 1505
• 8 Ledroit V, Debitus C, Lavaud C, Massiot G. Tetrahedron Lett. 2003; 44: 225

For reviews on pachastrissamine syntheses, see:
• 9a Ballereau S, Baltas M, Genisson Y. Curr. Org. Chem. 2011; 15: 953
• 9b Abraham E, Davies SG, Roberts PM, Russell AJ, Thomson JE. Tetrahedron: Asymmetry 2008; 19: 1027

For recent syntheses of pachastrissamine, see:
• 10a Zhao M.-L, Zhang E, Gao J, Zhang Z, Zhao Y.-T, Qu W, Liu H.-M. Carbohydr. Res. 2012; 351: 126
• 10b Cruz-Gregorio S, Espinoza-Rojas C, Quintero L, Sartillo-Piscil F. Tetrahedron Lett. 2011; 52: 6370
• 10c Passiniemi M, Koskinen AM. P. Org. Biomol. Chem. 2011; 9: 1774
• 10d Lee HJ, Lim CM, Hwang SH, Jeong BS, Kim SH. Chem.–Asian J. 2011; 6: 1943
• 10e Llaveria J, Diaz Y, Matheu MI, Castillon S. Eur. J. Org. Chem. 2011; 1514
• 10f Yoshimitsu Y, Inuki S, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2010; 75: 3843
• 10g Vichare P, Chattopadhyay A. Tetrahedron: Asymmetry 2010; 21: 1983
• 10h Urano H, Enomoto M, Kuwahara S. Biosci. Biotechnol., Biochem. 2010; 74: 152
• 10i Inuki S, Yoshimitsu Y, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2010; 75: 3831
• 10j Inuki S, Yoshimitsu Y, Oishi S, Fujii N, Ohno H. Org. Lett. 2009; 11: 4478
• 10k Canals D, Mormeneo D, Fabrias G, Llebaria A, Casas J, Delgado A. Bioorg. Med. Chem. 2009; 17: 235
• 11a Salma Y, Lafont E, Therville N, Carpentier S, Bonnafe M.-J, Levade T, Genisson Y, Andrieu-Abadie N. Biochem. Pharmacol. 2009; 78: 477
• 11b Canals D, Mormeneo D, Fabrias G, Llebaria A, Casas J, Delgado A. Bioorg. Med. Chem. 2009; 17: 235
• 12a Kim JY, Mu Y, Jin XD, Park SH, Pham VT, Song DK, Lee KY, Ham WH. Tetrahedron 2011; 67: 9426
• 12b Pham VT, Joo JE, Lee KY, Kim TW, Mu Y, Ham WH. Tetrahedron 2010; 66: 2123
• 13a Joo JE, Pham VT, Tian YS, Chung YS, Lee KY, Ham WH. Org. Biomol. Chem. 2008; 6: 1498
• 13b Joo JE, Lee KY, Pham VT, Ham WH. Eur. J. Org. Chem. 2007; 1586
• 13c Joo JE, Lee KY, Pham VT, Tian YS, Ham WH. Org. Lett. 2007; 9: 3627
• 14a Schwab PE, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1996; 118: 100
• 14b Scholl M, Trnka TM, Morgan JP, Grubbs RH. Tetrahedron Lett. 1999; 40: 2247
• 14c Love JA, Sanford MS, Day MW, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 10103
• 14d Lombardo M, Capdevila MG, Pasi F, Trombini C. Org. Lett. 2006; 8: 3303
• 14e Singh OV, Kampf DJ, Han H. Tetrahedron Lett. 2004; 45: 7239
• 14f Perali RS, Mandava S, Chalapala S. Tetrahedron 2011; 67: 9283
• 14g Tian YS, Joo JE, Pham VT, Lee KY, Ham WH. Arch. Pharm. Res. 2007; 30: 167
• 14h Pham VT, Joo JE, Tian YS, Oh CY, Ham WH. Arch. Pharm. Res. 2007; 30: 22
• 15 The synthesis of pachastrissamine (2) was achieved in three steps from N-Boc-triol 3: Ribes C, Falomir E, Carda M, Marco JA. Tetrahedron 2006; 62: 5421