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Volumn 6, Issue 11, 2004, Pages 1749-1752

Application of enantioselective radical reactions: Synthesis of (+)-ricciocarpins A and B

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; MOLLUSCACIDE; ORGANOMETALLIC COMPOUND; OXAZOLIDINONE DERIVATIVE; RADICAL; RICCIOCARPIN A; RICCIOCARPIN B; UNCLASSIFIED DRUG;

EID: 2942538586     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0495772     Document Type: Article
Times cited : (37)

References (45)
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    • For recent reviews see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263. (b) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8303.
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    • For recent reviews see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263. (b) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8303.
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    • Racemic synthesis: (a) Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737. (b) Takeda, K.; Ohkawa, N.; Hori, K.; Koizumi, T.; Yoshii, E. Heterocycles 1998, 47, 277.
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    • note
    • A similar disconnection has been applied in the racemic synthesis of 1 starting with 3 (or a slight variant) and 3-furyllithium (see refs 5b-e). The yield for this transformation has been <30%.
  • 27
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    • These compounds were prepared in a straightforward fashion using well-established literature procedures. See Supporting Information for details
    • These compounds were prepared in a straightforward fashion using well-established literature procedures. See Supporting Information for details.
  • 28
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    • See Supporting Information for details
    • See Supporting Information for details.
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    • note
    • 2 has been previously shown to provide products with R configuration. We initially assigned the stereochemistry for 16 on the basis of the above precedents, which was later confirmed by the synthesis of the natural product.
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    • note
    • Attempts to form the six-membered ring with an acyl-oxazolidinone (instead of the methyl ester) gave complex product mixtures.
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    • note
    • d = 3.6 Hz, 1H). The 12 Hz coupling constant clearly establishes the relative stereochemistry at the ring as trans.
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    • note
    • Temperature of the reaction is important to avoid the premature formation of the lactone.
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    • For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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    • For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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    • For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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    • For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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