Stereoselective trans- and cis-dihydroxylations of 2H-pyranyl and dihydropyridinyl heterocycles synthesized from formal [3 + 3]-cycloaddition reactions of α,β-unsaturated iminium ions with 1,3-dicarbonyl equivalents

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2141-2144

  Zehnder, Luke R ^a   Wei, Lin Li ^a   Hsung, Richard P ^a   Cole, Kevin P ^a   McLaughlin, Michael J ^a   Shen, Hong C ^a   Sklenicka, Heather M ^a   Wang, Jiashi ^a   Zificsak, Craig A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKENE; ARISUGACIN A; ARISUGACIN H; CYCLOHEXANONE; CYCLOHEXANONE DERIVATIVE; FUSED HETEROCYCLIC RINGS; IMINE; LEPADIN A; OREVACTAENE; PYRAN DERIVATIVE; PYRIDINE DERIVATIVE; PYRONE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKALOIDS; ALKENES; CATALYSIS; CYCLOHEXANONES; HETEROCYCLIC COMPOUNDS, 2-RING; HYDROXYLATION; IMINES; MOLECULAR STRUCTURE; PYRANS; PYRIDINES; PYRONES; QUINOLINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035850284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010034r     Document Type: Article

References (48)

1. After the corresponding author, all author names are listed alphabetically.
2. There are a limited number of examples of metal-mediated [3 + 3]-cycloaddition reactions. For recent reviews, see: (a) Frühauf, H.-W. Chem. Rev. 1997, 97, 523.
3. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
4. For recent reviews on stepwise [3 + 3] formal cycloaddition, see: (a) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27-76.
5. (b) Rappoport, Z. The Chemistry of Enamines. In The Chemistry of Functional Groups; John Wiley and Sons: New York, 1994.
6. Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Shen, H. C.; McLaughlin, M. J.; Zehnder, L. R. Submitted.
7. (a) McLaughlin, M. J.; Shen, H. C.; Hsung, R. P. Tetrahedron Lett. 2001, 42, 609.
8. (b) Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org. Chem. 1999, 64, 690.
9. (a) Wei, L.-L.; Sklenicka, H. M.; Gerasyuto, A. I.; Hsung, R. P. Angew. Chem., Int. Ed. 2001, 40, 1516.
10. (b) Sklenicka, H. M.; Hsung, R. P.; Wei, L.-L.; McLaughlin, M. J.; Gerasyuto, A. I.; Degen., S. J.; Mulder, J. A. Org. Lett. 2000, 2, 1161.
11. Hsung, R. P.; Wei, L.-L.; Sklenicka, H. M.; Douglas, C. J.; McLaughlin, M. J.; Mulder, J. A.; Yao, L. J. Org. Lett. 1999, 1, 509.
12. For some recent notable studies in this area, see: (a) Cravotto, G.; Nano, G. M.; Tagliapietra, S. Synthesis 2001, 49.
13. (b) Hua, D. H.; Chen, Y.; Sin, H.-S.; Robinson, P. D.; Meyers, C. Y.; Perchellet, E. M.; Perchellet, J.-P.; Chiang, P. K.; Biellmann, J.-P. Acta Crystallogr. 1999, C55, 1698.
14. P. Benovsky, G. A. Stephenson, J. R. Stille, J. Am. Chem. Soc. 1998, 120, 2493.
15. (a) Shishido, K.; Ito, M.; Shimada, S.-I.; Fukumoto, K.; Kametani, T. Chem. Lett. 1984, 1943.
16. (b) Maynard, D. F.; Okamura, W. H. J. Org. Chem. 1995, 60, 1763.
17. (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
18. (b) Tietze, L. F. J. Heterocycl. Chem. 1990, 27, 47.
19. For a leading reference, see: Otoguro, K.; Shiomi, K.; Yamaguchi, Y.; Arai, N.; Sunazuka, T.; Masuma, R.; Iwai, Y.; Õmura, S. J. Antibiot. 2000, 53, 50.
20. Zehnder, L. R.; Hsung, R. P.; Wang, J.-S.; Golding, G. M. Angew. Chem., Int. Ed. 2000, 39, 3876.
21. For our other approaches related to the synthesis of arisugacin, see: (a) Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901.
22. (b) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 39, 9597.
23. Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
24. (a) Steffan, B. Tetrahedron 1991, 41, 8729.
25. (b) Kubanek, J.; Williams, D. E.; de silva, E. D.; Allen, T.; Andersen, R. J. Tetrahedron Lett. 1995, 36, 6189.
26. Ozawa, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2000, 2, 2955.
27. Toyooka, N.; Okumura, M.; Takahata, H. J. Org. Chem. 1999, 64, 2182.
28. (a) Shu, Y.-Z.; Ye, Q.; Li, H.; Kadow, K. F.; Hussain, R. A.; Huang, S.; Gustavson, D. R.; Lowe, S. E.; Chang, L. P.; Pirnik, D. M.; Kodukula, K. Bioorg. Med. Chem. Lett. 1997, 17, 22295.
29. (b) Organ, M. G.; Bratovanov, S. Tetrahedron Lett. 2000, 41, 6945.
30. For some examples, see: (a) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
31. (b) Yorozu, K.; Takai, T. Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1994, 67, 2195.
32. Vander Velde, S. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 5380.
33. (a) Costes, N.; Michel, S.; Tillequin, F.; Koch, M.; Pierré, A.; Atassi, G. J. Nat. Prod. 1999, 62, 490.
34. (b) David, M.; Boustie, J.; Peilloux, A.; Poupon, E.; Amoros, M.; Sauleau, A. Pharm. Sci. 1997, 5, 305.
35. (a) Brown, R. F. C.; Hobbs, J. J.; Hughs, G. K.; Richie, E. Aust. J. Chem. 1954, 7, 348 and 374.
36. (b) Watters, W. H.; Ramachandran, V. N. J. Chem. Res., Miniprint 1997, 6, 1201.
37. 13C NMR, FTIR, and mass spectroscopy.
38. cis/trans-Isomers of diol 14 or 15 were isolated under some of these conditions.
39. Appendino, G.; Cravotto, G.; Nano, G. M.; Palmisano, G.; Annunzata, R. Helv. Chim. Acta 1993, 76, 1194.
40. Lau, C. K.; Defresne, C.; Belanger, P. C.; Pietre, S.; Scheigetz, J. J. Org. Chem. 1986, 51, 3038.
41. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1999, 64, 4790.
42. The absolute stereochemistry of 19-cis and ent-19-cis were assigned on the basis of Sharpless' mnemonics, see: Wang, Z.-M.; Kakiuchi, K.; Sharpless, K. B. J. Org. Chem. 1994, 59, 6895.
43. 2 followed by DIBAL-H did not provide the desired monohydroxylated products.
44. (a) Burns, C. J.; Gill, M.; Saubern, S. Aust. J. Chem. 1991, 44, 1427.
45. (b) Rodriguez-Hahn, L.; Esquivel, B.; Sanchez, C.; Estebanes, L.; Cardenas, J. Phytochemistry 1989, 28, 567.
46. Carey, F. A.; Tremper, H. S. J. Org. Chem. 1971, 36, 758.
47. (a) Rho, H.-S.; Ko, B.-S. Synth. Commun. 1999, 29, 2875.
48. 3SnH was not used as solvent or in large excess.