A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

For excellent reviews on the natural occurrence and therapeutic applications of azasugars, see: Look, 1993, Acc. Chem. Res., 26, 182, 10.1021/ar00028a008 Ganem, 1996, Acc. Chem. Res., 29, 340, 10.1021/ar9502184 Watson, 2001, Phytochemistry, 56, 265, 10.1016/S0031-9422(00)00451-9 Wroding, 2002, Monatsh. Chem., 133, 393, 10.1007/s007060200018 Asano, 2005, Tetrahedron: Asymmetry, 11, 1645, 10.1016/S0957-4166(00)00113-0 Legler, 1998 Horii, 1986, J. Med. Chem., 29, 1038, 10.1021/jm00156a023 Fischer, 1995, J. Virol., 69, 5791, 10.1128/JVI.69.9.5791-5797.1995 Furukawa, 1985, Phytochemistry, 24, 593, 10.1016/S0031-9422(00)80773-6 Nash, 1985, Phytochemistry, 24, 1620, 10.1016/S0031-9422(00)81084-5 Jones, 1985, Tetrahedron Lett., 26, 3125, 10.1016/S0040-4039(00)98635-0 Fleet, 1985, Tetrahedron Lett., 26, 3127, 10.1016/S0040-4039(00)98636-2 Scofield, 1986, Life Sci., 39, 645, 10.1016/0024-3205(86)90046-9 Axamawaty, 1990, Biochem. J., 266, 245, 10.1042/bj2660245 Mackay, 2003, Diabetes Obes. Metab., 5, 397, 10.1046/j.1463-1326.2003.00293.x Fleet, 1988, FEBS Lett., 237, 128, 10.1016/0014-5793(88)80185-6 Karpas, 1988, Proc. Natl. Acad. Sci. U.S.A., 85, 9229, 10.1073/pnas.85.23.9229 Shibata, 1988, J. Antibiot., 41, 296, 10.7164/antibiotics.41.296 Kayakiri, 1988, Tetrahedron Lett., 29, 1725, 10.1016/S0040-4039(00)82028-6 Ysujii, 1996, Biochem. Biophys. Res. Commun., 220, 459, 10.1006/bbrc.1996.0427 Yasuda, 2002, J. Nat. Prod., 65, 198, 10.1021/np010360f Buku, 1980, Proc. Natl. Acad. Sci. U.S.A., 77, 2370, 10.1073/pnas.77.5.2370 Faulstich, 1980, Biochemistry, 19, 3334, 10.1021/bi00555a036 Dondoni, 2002, J. Org. Chem., 67, 7203, 10.1021/jo020252d Welter, 1976, Phytochemistry, 15, 747, 10.1016/S0031-9422(00)94435-2 Nash, 1996, Vol. 11, 345 Molyneux, 1993, J. Nat. Prod., 56, 1356, 10.1021/np50098a020 Asano, 2001, Eur. J. Biochem., 268, 35, 10.1046/j.1432-1327.2001.01837.x Shibano, 2001, Chem. Pharm. Bull., 49, 1362, 10.1248/cpb.49.1362 Tsukamoto, 2001, Chem. Pharm. Bull., 49, 1487, 10.1248/cpb.49.1487 For revision of absolute configuration of radicamines, see: Yu, 2006, Org. Lett., 8, 3021, 10.1021/ol0609210 For reviews on the enantiomeric synthesis of 2-hydroxymethylpyrrolidine alkaloids, see: Ref. 1c; El-Ashry, 2003, Carbohydr. Res., 338, 2265, 10.1016/j.carres.2003.09.002 Ayad, 2004, Curr. Org. Chem., 8, 1211, 10.2174/1385272043370005 For some enantiospecific synthesis of DAB 1 (1), see: Fleet, 1986, Tetrahedron, 42, 5685, 10.1016/S0040-4020(01)88174-6 Ziegler, 1988, Angew. Chem., Int. Ed. Engl., 27, 716, 10.1002/anie.198807161 von der Osten, 1989, J. Am. Chem. Soc., 111, 3924, 10.1021/ja00193a025 Fleet, 1990, Tetrahedron: Asymmetry, 1, 119, 10.1016/S0957-4166(00)86337-5 Hung, 1991, J. Org. Chem., 56, 3849, 10.1021/jo00012a015 Griffat-Brunet, 1994, Tetrahedron Lett., 35, 2889, 10.1016/S0040-4039(00)76651-2 Overkleeft, 1994, Tetrahedron, 50, 4215, 10.1016/S0040-4020(01)86715-6 Huwe, 1997, Synthesis, 61, 10.1055/s-1997-1497 Kim, 1997, Tetrahedron, 53, 7501, 10.1016/S0040-4020(97)00445-6 Ahn, 1997, Bull. Korean Chem. Soc., 18, 1192 Kim, 1998, J. Chem. Soc., Perkin Trans. 1, 2877, 10.1039/a803342k Hulme, 2000, J. Chem. Soc., Perkin Trans. 1, 1837, 10.1039/b002707n Ayad, 2003, Eur. J. Org. Chem., 2903, 10.1002/ejoc.200300163 Lauritsen, 2006, Org. Biomol. Chem., 4, 2898, 10.1039/b605818c For the enantioselective synthesis of LAB 1 (2), see: Ref. 15a; Behling, 1993, Tetrahedron, 49, 3359, 10.1016/S0040-4020(01)90163-2 Huang, 1997, J. Org. Chem., 62, 372, 10.1021/jo962028s Ref. 15i; Lombardo, 2001, J. Org. Chem., 66, 1264, 10.1021/jo0056545 For the enantiospecific synthesis of nectrisine (3), see: Chen, 1990, Tetrahedron Lett., 31, 2229, 10.1016/0040-4039(90)80192-O Kayakiri, 1991, Chem. Pharm. Bull., 39, 2807, 10.1248/cpb.39.2807 Takayam, 1997, J. Am. Chem. Soc., 119, 8146, 10.1021/ja971695f Kim, 1999, Tetrahedron, 55, 8353, 10.1016/S0040-4020(99)00459-7 Bosco, 2001, Tetrahedron Lett., 42, 7949, 10.1016/S0040-4039(01)01684-7 Tschamber, 2002, Eur. J. Org. Chem., 702, 10.1002/1099-0690(200202)2002:4<702::AID-EJOC702>3.0.CO;2-Y Hulme, 2003, Tetrahedron Lett., 44, 7649, 10.1016/j.tetlet.2003.08.030 For the enantiospecific synthesis of 6-deoxy-DMDP 7, see: Wang, 1993, Tetrahedron Lett., 34, 403, 10.1016/0040-4039(93)85087-D Ref. 12a; Bisseret, 1999, Org. Lett., 1, 1181, 10.1021/ol990841e Espelt, 2003, Chem.—Eur. J., 9, 4887, 10.1002/chem.200304966 Yoda, 1999, Tetrahedron Lett., 40, 1335, 10.1016/S0040-4039(98)02605-7 For some indirect hydroxymethylation methods, see: Barrett, 1991, J. Org. Chem., 56, 2787, 10.1021/jo00008a040 Kang, 1999, Tetrahedron: Asymmetry, 10, 657, 10.1016/S0957-4166(99)00030-0 Ref. 18; Smith, 1999, J. Am. Chem. Soc., 121, 10468, 10.1021/ja992134m Chen, 2004, Tetrahedron, 60, 10223, 10.1016/j.tet.2004.09.001 For two accounts, see: Huang, 2005, Recent Advances on the Asymmetric Synthesis of Bioactive 2-Pyrrolidinone-related Compounds Starting from Enantiomeric Malic Acid, 197 Huang, 2006, Synlett, 1133, 10.1055/s-2006-941565 Zheng, 2005, Org. Lett., 7, 553, 10.1021/ol047733z Wei, 2006, Tetrahedron, 62, 190, 10.1016/j.tet.2005.09.112 Zhou, 2006, Synlett, 1235 Zhou, X.; Ye, J.-L.; Huang, P.-Q. C. R. Chim., in press. For reviews on the use of both enantiomers of tartaric acid as chirons, see: Coppola, 1997 Gawronski, 1999 Ghosh, 2001, Synthesis, 1281, 10.1055/s-2001-15217 For previous reports on the reductive alkylation of O,O′-diTBS-tartarimide, see: Yoda, 1993, Tetrahedron: Asymmetry, 4, 1451, 10.1016/S0957-4166(00)80339-0 Yoda, 1993, Tetrahedron: Asymmetry, 4, 1455, 10.1016/S0957-4166(00)80340-7 Yoda, 1995, Heterocycles, 41, 2423, 10.3987/COM-95-7214 Yoda, 1996, Tetrahedron Lett., 37, 5531, 10.1016/0040-4039(96)01042-8 Jeong, 2002, J. Heterocycl. Chem., 39, 1019, 10.1002/jhet.5570390525 For an account, see: Yoda, 2002, Curr. Org. Chem., 6, 223, 10.2174/1385272024605069 Milosevic, 2005, Org. Lett., 7, 5023, 10.1021/ol0519902 For some hydroxymethylation methods, see: Still, 1978, J. Am. Chem. Soc., 100, 1481, 10.1021/ja00473a025 Corey, 1983, Tetrahedron Lett., 24, 3163, 10.1016/S0040-4039(00)88124-1 Imamoto, 1984, Tetrahedron Lett., 25, 3225, 10.1016/S0040-4039(01)91015-9 Sasaki, 1988, Tetrahedron Lett., 29, 4847, 10.1016/S0040-4039(00)80624-3 Nicotra, 1989, Gazz. Chim. Ital., 119, 577 Murakami, 1990, J. Am. Chem. Soc., 112, 2437, 10.1021/ja00162a064 Bols, 1992, J. Chem. Soc., Chem. Commun., 445, 10.1039/c39920000445 Kim, 2000, Tetrahedron, 56, 9319, 10.1016/S0040-4020(00)00847-4 Skrydstrup, 1996, Chem. Commun., 515, 10.1039/cc9960000515 For an excellent review, see: Kagan, 2003, Tetrahedron, 59, 10351, 10.1016/j.tet.2003.09.101 For a leading reference on the recent application of SmI2 in organic synthesis, see: Huang, 2006, J. Am. Chem. Soc., 128, 5624, 10.1021/ja061114z Girard, 1980, J. Am. Chem. Soc., 102, 2693, 10.1021/ja00528a029 For a review, see: Kursanov, 1974, Synthesis, 633, 10.1055/s-1974-23387 For selected examples, see: Drage, 1982, J. Heterocycl. Chem., 19, 701, 10.1002/jhet.5570190358 Hart, 1985, J. Org. Chem., 50, 235, 10.1021/jo00202a016 Rolf, 1982, J. Am. Chem. Soc., 104, 3539, 10.1021/ja00376a065 Thaning, 1989, Acta Chem. Scand., 43, 290, 10.3891/acta.chem.scand.43-0290 Thaning, 1990, J. Org. Chem., 55, 1406, 10.1021/jo00291a065 Jouin, 1990, J. Chem. Soc., Perkin Trans. 1, 1177 Bernardi, 1990, Tetrahedron Lett., 31, 4949, 10.1016/S0040-4039(00)97777-3 Koot, 1991, Tetrahedron Lett., 32, 401, 10.1016/S0040-4039(00)92639-X Huang, 1998, Tetrahedron, 54, 12547, 10.1016/S0040-4020(98)00734-0 Huang, 1998, Synth. Commun., 28, 417, 10.1080/00397919808005095 Oba, 2002, Tetrahedron, 58, 9359, 10.1016/S0040-4020(02)01218-8 For the situation of 2-oxazolidinone derivatives, see: Rich, 1980, J. Med. Chem., 23, 27, 10.1021/jm00175a006 He, 2003, Tetrahedron: Asymmetry, 14, 2101, 10.1016/S0957-4166(03)00442-7 Ye, 2007, J. Org. Chem., 72, 35, 10.1021/jo0613683 Yamaura, 1985, Bull. Chem. Soc. Jpn., 58, 1413, 10.1246/bcsj.58.1413 Yoshimura, 1983, Chem. Lett., 1001, 10.1246/cl.1983.1001 Yoda, 1996, Tetrahedron: Asymmetry, 7, 373, 10.1016/0957-4166(96)00009-2 Kanazawa, 1998, J. Org. Chem., 63, 4660, 10.1021/jo9801162 Huang, 2003, Org. Lett., 5, 4341, 10.1021/ol035617a For recent reviews on the chemistry of N-acyliminium ions, see: Speckamp, 2000, Tetrahedron, 56, 3817, 10.1016/S0040-4020(00)00159-9 Bur, 2001, Tetrahedron, 57, 3221, 10.1016/S0040-4020(01)00035-7 Maryanoff, 2004, Chem. Rev., 104, 1431, 10.1021/cr0306182 Royer, 2004, Chem. Rev., 104, 2311, 10.1021/cr020083x Gurjar, 2006, Tetrahedron Lett., 47, 6979, 10.1016/j.tetlet.2006.07.120 Liu, 2004, J. Org. Chem., 69, 6001, 10.1021/jo049166z Miles, 1999, Biochemistry, 38, 13147, 10.1021/bi990829u Severino, 2003, Org. Lett., 5, 305, 10.1021/ol027268a For a review on the oxidative degradation of benzene rings, see: Mander, 2003, Tetrahedron, 59, 1105, 10.1016/S0040-4020(02)01492-8 For an example of using oxidative degradation of p-methoxyphenyl group (into a carboxyl group) in the asymmetric synthesis of DMDP, see: Garcia, 2003, Tetrahedron Lett., 44, 1553, 10.1016/S0040-4039(03)00017-0 Smith, 2004, Org. Lett., 6, 2063, 10.1021/ol0492647 Larsen, 2005, J. Am. Chem. Soc., 127, 10879, 10.1021/ja0524043 For selected examples in N-acyliminium series, see: Renaud, 1986, Helv. Chim. Acta, 69, 1704, 10.1002/hlca.19860690726 Yoda, 1995, Tetrahedron: Asymmetry, 6, 2669, 10.1016/0957-4166(95)00353-Q Boto, 2000, J. Org. Chem., 65, 4930, 10.1021/jo000356t Brenneman, 2004, Org. Lett., 6, 1329, 10.1021/ol049631e Oba, 2004, Angew. Chem., Int. Ed., 43, 2412, 10.1002/anie.200353366 Meza-León, 2004, J. Org. Chem., 69, 3976, 10.1021/jo049757p Ceccon, 2005, Synlett, 1413 For other approaches to DHP, see: Arakawa, 1991, Chem. Pharm. Bull., 39, 2219, 10.1248/cpb.39.2219 Taylor, 2002, J. Org. Chem., 67, 4466, 10.1021/jo025538x