Asymmetric synthesis of sesaminone: Confirmation of its structure and determination of its absolute configuration

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7413-7417

  Maioli, Andrew T ^a   Civiello, Rita L ^a   Foxman, Bruce M ^a   Gordon, Dana M ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGNAN; NATURAL PRODUCT; SESAMINONE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG STRUCTURE; DRUG SYNTHESIS; ISOLATION PROCEDURE; REDUCTION; STEREOCHEMISTRY; STREPTOMYCES;

EID: 0030786722     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971027c     Document Type: Article

References (29)

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8. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
9. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
10. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
11. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
12. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
13. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
14. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
15. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
16. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
17. For entry into the literature on the formation of carbon-carbon bonds utilizing acetals as a source of electrophilic carbon and the mechanisms of these reactions, see: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 5. (b) Overman, L. E.; Castañeda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043. (d) Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107. (e) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477. (f) Denmark, S. E.; Almstead, N. J. Org. Chem. 1991, 56, 6458. (g) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354. (h) Denmark, S. E.; Almstead, N. J. Am. Chem. Soc. 1991, 113, 8089. (i) Sammakia, T.; Smith, R. S. J. Org. Chem. 1992, 57, 2997. (j) Overman, L. E. Acc. Chem. Res. 1992, 25, 352. (k) Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958.
18. For examples of this preference in systems where one of the vicinal stereocenters has been equilibrated via an enolate to give the trans product as the major diastereomer, see: (a) Frauenrath, H.; Runsink, J. J. Org. Chem. 1987, 52, 2707. (b) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354.
19. For examples of this preference in systems where one of the vicinal stereocenters has been equilibrated via an enolate to give the trans product as the major diastereomer, see: (a) Frauenrath, H.; Runsink, J. J. Org. Chem. 1987, 52, 2707. (b) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354.
20. For a general review and a checked experimental procedure, see: (a) Evans, D. A. Aldrichimica Acta 1982, 15, 23. (b) Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 83.
21. For a general review and a checked experimental procedure, see: (a) Evans, D. A. Aldrichimica Acta 1982, 15, 23. (b) Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 83.
22. Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F., Jr. Tetrahedron 1988, 44, 5525.
23. Penning, T. D.; Djuric, S. W.; Haack, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowell, B. W.; Yu, S. S. Synth. Commun. 1990, 20, 307.
24. Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1984, 25, 5953.
25. Various aryl ketones have been converted under similar reaction conditions to mixtures of TBDMS enol ethers enriched in the Z stereoisomer, see: Snider, B. B.; Kwon, T. J. Org. Chem. 1992, 57, 2399.
26. (a) Linderman, R. J.; Godfrey, A. J. Am. Chem. Soc. 1988, 110, 6249.
27. (b) Linderman, R. J.; Graves, D. M.; Kwochka, W. R.; Ghannam, A. F.; Anklekar, T. V. J. Am. Chem. Soc. 1990, 112, 7438.
28. (c) Linderman, R. J.; Anklekar, T. V. J. Org. Chem. 1992, 57, 5078.
29. The authors have deposited atomic coordinates for structure 1 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, U. K.