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Volumn 128, Issue 51, 2006, Pages 16720-16732

Total synthesis and evaluation of cytostatin, its C10-C11 diastereomers, and additional key analogues: Impact on PP2A inhibition

Author keywords

[No Author keywords available]

Indexed keywords

CYTOSTATIN; DIASTEREOMERS; NUCLEOPHILIC ADDITION; STEREOSELECTIVITY;

EID: 33845928989     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066477d     Document Type: Article
Times cited : (53)

References (77)
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    • (a) Sultriecin: Ohkuma, H.; Naruse, N.; Nishiyama, Y.; Tsuno, T.; Hoshino, Y.; Sawada, Y.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1239.
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    • (c) Leustroducsins: Kohama, T.; Enokita, R.; Okazaki, T.; Miyaoka, H.; Torikata, A.; Inukai, M.; Kaneko, I.; Kagasaki, T.; Sakaida, Y.; Satoh, A.; Shiraishi, A. J. Antibiot. 1993, 46, 1503.
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    • (d) Phoslactomycins: Fushimi, S.; Nishikawa, S.; Shimazu, A.; Seto, H. J. Antibiot. 1989, 42, 1019.
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    • (e) Phosphazomycins: Tomiya, T.; Uramoto, M.; Isono, K. J. Antibiot. 1990, 43, 118.
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    • and ref 2. For reviews of fostriecin total syntheses see: a
    • For reviews of fostriecin total syntheses see: (a) Shibasaki, M.; Kanai, M. Heterocycles 2005, 66, 727 and ref 2.
    • (2005) Heterocycles , vol.66 , pp. 727
    • Shibasaki, M.1    Kanai, M.2
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    • Similar coupling patterns have been reported for other 4,5-disubstituted-α,β-unsaturated lactones: (a) Ley, S. V.; Armstrong, A.; Diez-Martin, D.; Ford, M. J.; Grice, P.; Knight, J. G.; Kolb, H. C.; Madin, A.; Marby, C. A.; Mukherjee, S.; Shaw, A. N.; Slawin, A. M.; Vile, S.; White, A. D.; Williams, D. J.; Woods, M. J. Chem. Soc., Perkin 1 1991, 667.
    • Similar coupling patterns have been reported for other 4,5-disubstituted-α,β-unsaturated lactones: (a) Ley, S. V.; Armstrong, A.; Diez-Martin, D.; Ford, M. J.; Grice, P.; Knight, J. G.; Kolb, H. C.; Madin, A.; Marby, C. A.; Mukherjee, S.; Shaw, A. N.; Slawin, A. M.; Vile, S.; White, A. D.; Williams, D. J.; Woods, M. J. Chem. Soc., Perkin 1 1991, 667.
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    • 14d
    • 14d
  • 50
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    • The trans-Cl stereochemistry was assigned on the basis of H3-H4 coupling (J = 6.0 Hz). Similar trans-1,4-disubstituted dihydropyrans display an H3-H4 coupling (J = 5.7 Hz) distinct from that of cis-1,4-disubstituted dihydropyrans (J = 1.9 Hz). See: Valverde. S.; Bernabe, M.; Garcia-Ochoa, S.; Gomez, A. M. J. Org. Chem. 1990, 55, 2294.
    • The trans-Cl stereochemistry was assigned on the basis of H3-H4 coupling (J = 6.0 Hz). Similar trans-1,4-disubstituted dihydropyrans display an H3-H4 coupling (J = 5.7 Hz) distinct from that of cis-1,4-disubstituted dihydropyrans (J = 1.9 Hz). See: Valverde. S.; Bernabe, M.; Garcia-Ochoa, S.; Gomez, A. M. J. Org. Chem. 1990, 55, 2294.
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    • Lipshutz, B. H.; Moretti, R.; Crow, R. Organic Syntheses; Wiley: New York, 1993; Collect. VIII, p 33.
    • Lipshutz, B. H.; Moretti, R.; Crow, R. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. VIII, p 33.
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    • Structure of DiFMUP: [Diagram presented]
    • Structure of DiFMUP: [Diagram presented]
  • 72
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    • rhPP1α was expressed in E. coli with the pKK-223-2 vector (accession no. M77749) and purified essentially as described: Zhang, L.; Lee, E. Y. Biochemistry 1997, 36, 8209.
    • rhPP1α was expressed in E. coli with the pKK-223-2 vector (accession no. M77749) and purified essentially as described: Zhang, L.; Lee, E. Y. Biochemistry 1997, 36, 8209.


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