Studies towards the synthesis of the C29-C51 fragment of altohyrtin A

Synlett

Volumn , Issue 9, 1998, Pages 991-994

  Fernandez Megia, Eduardo ^a   Gourlaouen, Nelly ^a   Ley, Steven V ^a   Rowlands, Gareth J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000200913     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-3140     Document Type: Article

References (46)

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20. During the course of this research Smith and coworkers have published the synthesis of the same fragment 31 without the SEM protecting group at the C47 hydroxy group, and have demonstrated that it displays significant in vitro activity against five human cancer cell lines: Smith, A. B., III; Lin, Q.; Pettit, G. R.; Chapuis, J.-C.; Schmidt, J. M. Bioorg. Med. Chem. Lett. 1998, 8, 567.
21. Altohyrtin A numbering.
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29. 3, 600 MHz) δ 7.34-7.21 (15H, m), 5.04 (1H, brs), 4.90 (1H, d, J 11.0 Hz), 4.82 (1H, d, J 11.0 Hz), 4.67 (1H, d, J 11.0 Hz), 4.56 (1H, brs), 4.52 (1H, d, J 11.0 Hz), 4.49 (1H, d, J 12.0 Hz), 4.44 (1H. d, J 12.0 Hz), 4.19 (1H, brd, J 9.0 Hz), 4.10 (1H, brd, J 7.5 Hz), 3.86 (1H, m), 3.77 (1H. m), 3.73-3.70 (2H, m), 3.66 (1H, d, J 10.0 Hz), 3.53 (1H, t, J 8.5 Hz), 3.49-3.43 (2H, m), 3.36-3.33 (3H, m), 3.28 (1H, brt, J 9.5 Hz), 2.24 (1H, d, J 12.0 Hz), 2.14-2.09 (2H, m), 1.81-1.75 (1H, m), 1.72-1.66 (2H, m), 1.65-1.59 (2H, m), 1.58-1.40 (6H, m), 1.33-1.24 (3H. m), 0.99 (3H, d, J 6.5 Hz), 0.82 (3H, d, J 7.0 Hz).
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33. 3, 200 MHz) δ 9.70 (1H, d, J 7.5 Hz), 7.13 (1H, d, J 15.1 Hz), 6.53 (1H, dd, J 7.5 Hz, J 15.1 Hz), 5.84 (1H, s), 5.82 (1H, d, J 1.0 Hz).
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45. Prepared according to Lombardo, L. Org. Synth. Coll. 1993, 8, 386.
46. 3, 600 MHz) δ 7.36-7.28 (15H, m), 6.23 (1H, d, J 15.0 Hz), 6.00 (1H, dd, J 7.2 Hz, J 15.0 Hz), 5.35 (1H, s), 5.29 (1H, s), 4.98 (1H, d, J 10.8 Hz), 4.93-4.91 (3H, m), 4.80 (1H, d, J 10.6 Hz), 4.79 (1H, d, J 12.2 Hz), 4.67-4.59 (4H, m), 4.53 (1H, d, J 3.5 Hz), 4.31 (1H, c, J 6.9 Hz), 3.98 (1H, t, J 9.2 Hz), 3.78 (1H, t, J 9.9 Hz), 3.68-3.64 (1H, m), 3.53-3.48 (2H, m), 3.34 (3H, s), 3.19 (1H, t, J 9.1 Hz), 2.63 (1H, d, J 13.9 Hz). 2.42 (1H, dd, J 7.5 Hz, J 14.1 Hz), 2.30 (1H, dd, J 5.9 Hz, J 14.1 Hz), 2.07 (1H, dd, J 10.0 Hz, J 14.1 Hz), 0.93-0.87 (2H, m), 0.00 (9H, s).