Concise and divergent total synthesis of swainsonine, 7-alkyl swainsonines, and 2,8a-diepilentiginosine via a chiral heterocyclic enaminoester intermediate

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 5005-5012

  Shi, Gao Feng ^a   Li, Jia Qi ^a   Jiang, Xiao Ping ^a   Cheng, Ying ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

Author keywords

2,8a Diepilentiginosine; Heterocyclic enaminoester; Polyhydroxylated indolizidine; Swainsonine; Total synthesis

Indexed keywords

1,2 DIHYDROXY 1,2,3,5 TETRAHYDRO 5 INDOLIZINONE; 1,2 DIHYDROXY 5 INDOLIZINONE; 1,2 O ISOPROPYLIDENEDIOXY 1,2,3,5 OCTAHYDRO 5 INDOLIZINONE; 1,2 O ISOPROPYLIDENEDIOXY 1,2,3,5 TETRAHYDRO 5 INDOLIZINONE; 1,2 O ISOPROPYLIDENEDIOXY 7 ISOBUTYL OCTAHYDRO 5 INDOLIZINONE 8 CARBOXYLIC ACID; 1,2 O ISOPROPYLIDENEDIOXY 7 METHYL OCTAHYDRO 5 INDOLIZINONE 8 CARBOXYLIC ACID; 1,2 O ISOPROPYLIDENEDIOXY 8 HYDROXYL 7 ISOBUTYL OCTAHYDRO 5 INDOLIZINONE; 1,2 O ISOPROPYLIDENEDIOXY 8 HYDROXYL 7 METHYL OCTAHYDRO 5 INDOLIZINONE; 1,2 O ISOPROPYLIDENEDIOXY 8 HYDROXYL 7 PROPYL OCTAHYDRO 5 INDOLIZINONE; 1,2 O ISOPROPYLIDENEDIOXY 8 HYDROXYL OCTAHYDRO 5 INDOLIZINONE; 1,2 O ISOPROPYLIDENEDIOXY OCTAHYDRO 5 INDOLIZINONE 8 CARBOXYLIC ACID; 2,8A DIEPILENTIGINOSINE; 5 INDOLIZINONE 8 CARBOXYLATE; 7 ISOBUTYL SWAINSONINE; 7 METHYL SWAINSONINE; 7 PROPYL SWAINSONINE; CARBOXYL GROUP; METHYL 1,2 O ISOPROPYLIDENEDIOXY 1,2,3,5 TETRAHYDRO 5 INDOLIZINONE 8 CARBOXYLATE; METHYL 1,2 O ISOPROPYLIDENEDIOXY 7 ISOBUTYL 1,2,3,5 TETRAHYDRO 5 INDOLIZINONE 8 CARBOXYLATE; METHYL 1,2 O ISOPROPYLIDENEDIOXY 7 ISOBUTYL OCTAHYDRO 5 INDOLIZINONE 8 CARBOXYLATE; METHYL 1,2 O ISOPROPYLIDENEDIOXY 7 PROPYL 1,2,3,5 TETRAHYDRO 5 INDOLIZINONE 8 CARBOXYLATE; METHYL 1,2 O ISOPROPYLIDENEDIOXY 7 PROPYL OCTAHYDRO 5 INDOLIZINONE 8 CARBOXYLATE; SWAINSONINE DERIVATIVE; TETRAHYDRO 5 INDOLIZINONE 8 CARBOXYLATE;

ANNULATION REACTION; ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 42749097497     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.080     Document Type: Article

References (55)

1. Michael J.P. Nat. Prod. Rep. 22 (2005) 603
2. Michael J.P. Nat. Prod. Rep. 21 (2004) 625
3. Pastuszak I., Molyneux R.J., James L.F., and Elbein A.D. Biochemistry 29 (1990) 1886
4. Yoda H., Katoh H., Ujihara Y., and Takabe K. Tetrahedron Lett. 42 (2001) 2509
5. Harris T.M., Harris C.M., Hill J.E., Ungemach F.S., Broquist H.P., and Wickwire B.M. J. Org. Chem. 52 (1987) 3094
6. Haraguchi M., Gorniak S.L., Ikeda K., Minami Y., Kato A., Watson A.A., Nash R.J., Molyneux R.J., and Asano N. J. Agric. Food Chem. 51 (2003) 4995
7. Guengerich F.P., DiMari S.J., and Broquist H.P. J. Am. Chem. Soc. 95 (1973) 2055
8. Schneider M.J., Ungemach F.S., Broquist H.P., and Harris T.M. Tetrahedron 39 (1983) 29
9. Hohenschultz L.D., Bell E.A., Jewess P.J., Leworthy D.P., Pryce R.J., Arnold E., and Clardy J. Phytochemistry 20 (1981) 811
10. Nash R.J., Fellows L.E., Dring J.V., Stirton C.H., Carter D., Hegarty M.P., and Bell E.A. Phytochemistry 27 (1988) 1403
11. Bastida A., Fernández-Mayoralas A., Arrayás R.G., Iradier F., Carretero J.C., and García-Junceda E. Chem.-Eur. J. (2001) 2390
12. Dwek R.A. Chem. Rev. 96 (1996) 683
13. Dorling P.R., Huxtable C.R., and Colegate S.M. Biochem. J. 191 (1980) 649
14. Liao Y.F., Lal A., and Moremen K.W. J. Biol. Chem. 271 (1996) 28348
15. Brandi A., Cicchi S., Cordero F.M., Frignoli R., Goti A., Picasso S., and Vogel P. J. Org. Chem. 60 (1995) 6806
16. Glick M.C., De Santis R., and Santer U.V. Prog. Clin. Biol. Res. 175 (1985) 229
17. De Gasperi R., Al Daher S., Winchester B.G., and Warren C.D. Biochem. J. 286 (1992) 55
18. Elbein A.D., Solf R., Dorling P.R., and Vosbeck K. Proc. Natl. Acad. Sci. U.S.A. 78 (1981) 7393
19. Schols D., Pauwels R., Witvrouw M., Desmyter J., and De Clercq E. Antiviral Chem. Chemother. 3 (1992) 23
20. Vlietinck A.J., De Bruyne T., Apers S., and Pieters L.A. Planta Med. 64 (1998) 97
21. Humphries M.J., Matsumoto K., White S.L., Molyneux R.J., and Olden K. Cancer Res. 48 (1988) 1410
22. Dennis J.W., White S.L., Freer A.M., and Dime D. Biochem. Pharmacol. 46 (1993) 1459
23. Bowen D., Southerland W.M., Bowen C.D., and Hughes D.E. Anticancer Res. 17 (1997) 4345
24. White S.L., Schweitzer K., Humphries M.J., and Olden K. Biochem. Biophys. Res. Commun. 150 (1988) 615
25. Yagita M., and Saksela E. Scand. J. Immunol. 31 (1990) 275
26. Kino T., Inamura N., Nakahara K., Kiyoto S., Goto T., Terano H., Kohsaka M., Aoki H., and Imanaka H. J. Antibiot. 38 (1985) 936
27. Dennis J.W. Cancer Res. 46 (1986) 5131
28. White S.L., Nagai T., Akiyama S.K., Reeves E.J., Grzegorzewski K., and Olden K. Cancer Commun. 3 (1991) 83
29. Dennis J.W. Semin. Cancer Biol. 2 (1991) 411
30. Roberts J.D., Klein J.L.D., Palmantier R., Dhume S.T., George M.D., and Olden K. Cancer Detect. Prev. 22 (1998) 455
31. Nemr A.E. Tetrahedron 56 (2000) 8579
32. Cardona F., Goti A., and Brandi A. Eur. J. Org. Chem. (2007) 1551
33. Cheng Y., Huang Z.-T., and Wang M.-X. Curr. Org. Chem. 8 (2004) 325
34. Jiang X.-P., Cheng Y., Shi G.-F., and Kang Z.-M. J. Org. Chem. 72 (2007) 2212
35. Buchanan J.G., Jigajinni V.B., Singh G., and Wightman R.H. J. Chem. Soc., Perkin Trans. 1 (1987) 2377
36. Buchanan J.G., Singh G., and Wightman R.H. J. Chem. Soc., Chem. Commun. (1984) 1299
37. Cohen N., Banner B.L., Lopresti R.J., Wong F., Rosenberger M., Liu Y.-Y., Thom E., and Liebman A.A. J. Am. Chem. Soc. 105 (1983) 3661
38. Denney D.B., and Sherman N. J. Org. Chem 30 (1965) 3760
39. Kienzle F., Holland G.W., Hernow J.L., Kwoh S., and Rosen P. J. Org. Chem. 38 (1973) 3440
40. Dannishefdky S., and Tsuzuki K. J. Am. Chem. Soc. 102 (1980) 6891
41. Suginome H., Ohue Y., and Orito K. J. Chem. Soc., Perkin Trans. 1 (1987) 1247
42. Marshall J.A., Andrews R.C., and Lebioda L. J. Org. Chem. 52 (1987) 2378
43. Trost B.M., and Patterson D.E. Chem.-Eur. J. 5 (1999) 3279
44. Fujimori K., and Oae S. J. Chem. Soc., Perkin Trans. 2 (1989) 1335
45. Taylor K.G., Govindan C.K., and Kaelin M.S. J. Am. Chem. Soc. 101 (1979) 2091
46. Kashiwagi T., and Oae S. Tetrahedron 26 (1970) 3631
47. Kashiwagi T., Kozuka S., and Oae S. Tetrahedron 26 (1970) 3619
48. Linhardt R.J., Murr B.L., Montgomery E., Osby J., and Sherbine J. J. Org. Chem. 47 (1982) 2242
49. Shiozaki M. Synthesis (1990) 691
50. Hatanaka M., and Ueda I. Chem. Lett. (1991) 61
51. Shiozaki M., Ishida N., and Sato S. Bull. Chem. Soc. Jpn. 62 (1989) 3950
52. Akhtar M., and Gani D. Tetrahedron 43 (1987) 5341
53. Marshall J.A., and Andrews R.C. Tetrahedron Lett. 27 (1986) 5197
54. CCDC 674145 (15B) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
55. Paolucci C., and Mattioli L. J. Org. Chem. 66 (2001) 4787