Synthesis of the C20-C26 Building Block of Halichondrins via a Regiospecific and Stereoselective SN2′ Reaction

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4427-4429

  Xie, Chaoyu ^a   Nowak, Pawel ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ETHERS, CYCLIC; STEREOISOMERISM;

EID: 0037069720     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026982p     Document Type: Article

References (39)

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6. For recent reviews on Cr-mediated reactions, see: (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (b) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1. (c) Saccomano, N. A. Comprehensive Organic Synhesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 1. p 173.
7. For recent reviews on Cr-mediated reactions, see: (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (b) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1. (c) Saccomano, N. A. Comprehensive Organic Synhesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 1. p 173.
8. For recent reviews on Cr-mediated reactions, see: (a) Fürstner, A. Chem. Rev. 1999, 99, 991. (b) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1. (c) Saccomano, N. A. Comprehensive Organic Synhesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 1. p 173.
9. 2,3
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14. For reviews relevant to this subject, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901. (b) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186.
15. (a) Gallina, C.; Ciattini, P. G. J. Am. Chem. Soc. 1979, 101, 1035.
16. (b) Gallina, C. Tetrahedron Lett. 1982, 23, 3093.
17. Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121.
18. In cyclic systems, allylic and homoallylic alcohols are known to direct the stereochemical course in conjugate additions of Grignard and cuprate reagents. For example, see: Fleming, F.; Guo, J.; Wang, Q.; Weaver, D. J. Org. Chem. 1999, 64, 8568 and references therein.
19. In the studies on asymmetric conjugate addition of organometallic reagents to α,β-unsaturated cyclic-diol monoesters, Sakai suggested a chelation complex involving a free hydroxy group and an ester carbonyl group: Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109 and references therein.
20. N2′ reactions, see: (a) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453. (b) Caló, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283. (c) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895. (d) Marino, J. P.; Viso, A. J. Org. Chem. 1991, 56, 1349. (e) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984. (f) Alexakis, A.; Mangeney, P.; Chribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. Pure Appl. Chem. 1988, 60, 49.
21. N2′ reactions, see: (a) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453. (b) Caló, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283. (c) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895. (d) Marino, J. P.; Viso, A. J. Org. Chem. 1991, 56, 1349. (e) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984. (f) Alexakis, A.; Mangeney, P.; Chribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. Pure Appl. Chem. 1988, 60, 49.
22. N2′ reactions, see: (a) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453. (b) Caló, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283. (c) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895. (d) Marino, J. P.; Viso, A. J. Org. Chem. 1991, 56, 1349. (e) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984. (f) Alexakis, A.; Mangeney, P.; Chribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. Pure Appl. Chem. 1988, 60, 49.
23. N2′ reactions, see: (a) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453. (b) Caló, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283. (c) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895. (d) Marino, J. P.; Viso, A. J. Org. Chem. 1991, 56, 1349. (e) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984. (f) Alexakis, A.; Mangeney, P.; Chribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. Pure Appl. Chem. 1988, 60, 49.
24. N2′ reactions, see: (a) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453. (b) Caló, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283. (c) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895. (d) Marino, J. P.; Viso, A. J. Org. Chem. 1991, 56, 1349. (e) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984. (f) Alexakis, A.; Mangeney, P.; Chribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. Pure Appl. Chem. 1988, 60, 49.
25. N2′ reactions, see: (a) Gais, H.-J.; Müller, H.; Bund, J.; Scommoda, M.; Brandt, J.; Raabe, G. J. Am. Chem. Soc. 1995, 117, 2453. (b) Caló, V.; Fiandanese, V.; Nacci, A.; Scilimati, A. Tetrahedron 1994, 50, 7283. (c) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895. (d) Marino, J. P.; Viso, A. J. Org. Chem. 1991, 56, 1349. (e) Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984. (f) Alexakis, A.; Mangeney, P.; Chribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. Pure Appl. Chem. 1988, 60, 49.
26. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
27. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1982, 23, 3093.
28. This coupling was possible without protection of propargyl alcohol but with slightly lower (ca. 70%) chemical yields.
29. The structure of 4 was assigned on comparison with the sample prepared by the Corey method: Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 4245. Because of the sluggishness of reaction and the relatively low chemical yield, we opted to use the hydrostannation route for the preparative purpose. The structures of the three minor products were not rigorously established. However, the chemical shifts of the vinyl protons suggested that the first, second, and third byproducts (the order of the amount formed) correspond to E-regioisomer, Z-isomer, and the Z-regioiosmer of 4, respectively. This tentative assignment was consistent with the observation that Z-isomer and Z-regioisomer formed a cyclic ether on the trisylation.
30. To the best of our knowledge, the first hydrostannylation of a propargyl group was reported by Neumann, Niermann, and Sommer in 1961 (Neumann, W. P.; Niermann, H.; Sommer, R. Angew. Chem. 1961, 73, 768). For the work relevant to this study, see: (a) Nativi, C.; Taddei, M. J. Org. Chem. 1988, 53, 820. (b) Ensley, H. E.; Buescher, R. R.; Lee, K. J. Org. Chem. 1982, 47, 404.
31. To the best of our knowledge, the first hydrostannylation of a propargyl group was reported by Neumann, Niermann, and Sommer in 1961 (Neumann, W. P.; Niermann, H.; Sommer, R. Angew. Chem. 1961, 73, 768). For the work relevant to this study, see: (a) Nativi, C.; Taddei, M. J. Org. Chem. 1988, 53, 820. (b) Ensley, H. E.; Buescher, R. R.; Lee, K. J. Org. Chem. 1982, 47, 404.
32. To the best of our knowledge, the first hydrostannylation of a propargyl group was reported by Neumann, Niermann, and Sommer in 1961 (Neumann, W. P.; Niermann, H.; Sommer, R. Angew. Chem. 1961, 73, 768). For the work relevant to this study, see: (a) Nativi, C.; Taddei, M. J. Org. Chem. 1988, 53, 820. (b) Ensley, H. E.; Buescher, R. R.; Lee, K. J. Org. Chem. 1982, 47, 404.
33. For a review on metal-catalyzed hydrostannations, see: Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257.
34. 2O), 2.7:1:1 (THF), 3.2:1:0.3 (THF/TMEDA), and 4.1:1:0 (DME), respectively, at -78 °C.
35. 2CuLi/DME/-78 °C, the substrates bearing a tosyl or camphorsulfonyl group in 5 gave a 4.1:1.0:0 (tosyl) or 6.0:1.0:0 (camphorsulfonyl) mixture of the desired product 6, the undesired C25 stereoisomer, and the undesired regioisomer.
36. Szeja, W. Synthesis 1979, 822.
37. This conclusion is based on the experiments conducted on i and ii. (Matrix Presented)
38. N2′ displacement did not give conclusive results.
39. The stereochemical purity was at least > 125:1 for the first crop obtained in the second recrystallization.