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Volumn 44, Issue 28, 2003, Pages 5259-5261

Efficient strategy for convergent synthesis of trans-fused polycyclic ethers based on an intramolecular SmI2-promoted cyclization of iodo ester

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROPYRAN; ESTER DERIVATIVE; ETHER DERIVATIVE; IODINE DERIVATIVE; LEWIS ACID; POLYCYCLIC AROMATIC COMPOUND; PYRAN DERIVATIVE; SAMARIUM DIIODIDE; SILANE; UNCLASSIFIED DRUG;

EID: 0037670118     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01277-2     Document Type: Article
Times cited : (15)

References (30)
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    • The iterative strategy for the synthesis of trans-fused polycyclic ethers via cyclic enol ether was also reported. For example, see: (a) Kozikowski, A. K.; Ghosh, A. K. J. Org. Chem. 1985, 50, 3017; (b) Bowman, J. L.; McDonald, F. E. J. Org. Chem. 1998, 63, 3680; (c) Rainier, J. D.; Allwein, S. P. Tetrahedron Lett. 1998, 39, 9601; (d) Cox, J. M.; Rainer, J. D. Org. Lett. 2001, 3, 2919; (e) Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron 2002, 58, 1997; (f) Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. J. Org. Chem. 2002, 67, 3494.
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    • note
    • 3) δ 138.18 (C-18), 137.91 (C-22), 128.39 (C-24 and 24′), 128.33 (C-20 and 20′), 127.90 (C-19 and 19′), 127.79 (C-23 and 23′), 127.75 (C-21), 127.60 (C-25), 80.46 (C-14), 78.32 (C-4), 77.21(C-5), 77.0 (C-7 and 8), 76.72 (C-10), 76.21 (C-11), 73.46 (C-16), 72.32 (C-13), 71.02 (C-17), 69.13 (C-15), 68.00 (C-1), 35.57 (C-6), 35.19 (C-9), 35.14 (C-12), 29.22 (C-3), 25.51 (C-2). The numbering was used as follows.


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