A total synthesis of (17S)-hexahydro-TMC-69

Heterocycles

Volumn 71, Issue 3, 2007, Pages 597-607

  Sugawara, Kazutoshi ^a   Imanishi, Yasuhiro ^a   Hashiyama, Tomiki ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547121194     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-06-10962     Document Type: Article

References (23)

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3. Contrast to the reported data sited in ref. l b), TMC-69-6H showed weak inhibitory activities towards cdc25A and cdc25B in the ref. 7b).
4. and literature cited therein. Nilsson I., and Hoffmann I. Progress in Cell Cycle Research 4 (2000) 107
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11. Fürstner A., Feyen F., Prinz H., and Waldmann H. Tetrahedron 60 (2004) 9543
12. Examples of pyridinone methide as reactive intermediates. Girotra N.N., and Wendler N.L. Heterocycles 9 (1978) 417
13. Titze L.F., Brands S., Brumby T., and Fennen J. Angew. Chem., Int. Ed. Engl. 29 (1990) 665
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15. See also ref. 13. Findlay J., Krepinsky J., Shum F.Y., and Tam W.H. Can. J Chem. 54 (1976) 270
16. Sugawara K., Imanishi Y., and Hashiyama T. Tetrahedron: Asymmetry 11 (2000) 4529
17. Synthesis of both the enantiomers of (6-methyloctyl)triphenylphosphonium bromide see. Bestmann H.G., Frighetto R.T.S., Frighetto N., and Vostrowsky O. Liebigs Ann. Chem. (1990) 829
18. When Pd/C was used instead of Ir-black, stereoselectivity decreased and an epimer was formed (ca. 10%).
19. Snider B.B., and Lu Q. J. Org. Chem. 61 (1996) 2839
20. H10, H11eq, = 1.7 Hz. and NOE analysis of 15 (see below) are in full accordance with the depicted configuration shown in Scheme 5. {A figure is presented} Representative observed NOE of 15
21. 20 = +88.6° (c = 0.95, McOH). The reason for this discrepancy is not clear, but purity of 1a may differ. According to the experimental section in the literature, it apparently does not include purification step after final N-hydroxylation reaction.
22. 13C-NMR analysis
23. 4), and concentrated in vacuo. Purification of the residue by column chromatography (33-66% AcOEt-hexane) gave 114 mg of 18 (94%) as colorless oil.