Studies toward the total synthesis of irumamycin: stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis

Tetrahedron Letters

Volumn 48, Issue 3, 2007, Pages 413-416

  Hirose, Tomoyasu ^a   Sunazuka, Toshiaki ^a   Yamamoto, Daisuke ^a   Mouri, Mutsumi ^a   Hagiwara, Yoshiaki ^a   Matsumaru, Takanori ^a   Kaji, Eisuke ^a   Omura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ALLYL COMPOUND; IRUMAMYCIN; NATURAL PRODUCT; VINYL DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DEPROTECTION REACTION; DRUG SYNTHESIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REDUCTION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 33845452462     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.079     Document Type: Article

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22. 3) δ: 7.24 (2H, d, J = 7.3 Hz), 6.83 (2H, d, J = 7.3 Hz), 5.88-5.64 (2H, complex m), 5.20-5.05 (4H, complex m), 4.64, 4.57 (each 1H, d, J = 10.2 Hz), 3.79 (3H, s), 3.31 (1H, dd, J = 5.4, 2.2 Hz), 2.35-2.24 (2H, m), 2.08-2.01 (2H, m), 1.06-0.91 (12H, m).
23. 3) analysis of 12. {A figure is presented}
24. 3, No. of observations (I > 0.00σ(I)) 1470; R 0.087; Rw 0.198. Crystallographic data of diol have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication Number CCDC 622750. Copies of the data can be obtained, free of charge, on application to CDCC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
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29. Group selective dihydroxylation of 17 using asymmetric catalysts. {A figure is presented}
30. 3) δ: 7.99 (2H, d, J = 8.6 Hz), 6.92 (2H, d, J = 8.6 Hz), 6.36 (1H, m), 5.86 (1H, ddd, J = 17.2, 10.2, 6.9 Hz), 5.06 (2H, complex m), 4.97 (1H, m), 3.87 (3H, s), 3.74 (1H, m), 2.70-2.49 (4H, m), 2.11-1.77 (5H, m), 1.77 (3H, s), 1.48-1.19 (2H, m), 1.13-0.90 (33H, complex m).