Total synthesis of antitumor antibiotic FR900482

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 55, Issue 11, 1997, Pages 946-957

  Katoh, Tadashi ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007052317     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.55.946     Document Type: Article

References (66)

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55. After purification by column chromatography on silica gel, the aliphatic segment 15 was immediately used for the next coupling reaction due to its instability.
56. When the corresponding mesylate and iodide were used as substrates for the subsequent coupling reaction with the aromatic segment 14, none of the desired product was obtained and the unreacted starting material was always recovered unchanged. To our delight, the triflate 15 was found to serve as an excellent electophile for the objective coupling reaction. For recent examples for the usefulness of some trifrate derivatives as good electrophiles, see, a) Fairbanks, A. J.; Fleet, G. W. J. Tetrahedron, 1995, 51, 3881.
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61. 1H-NMR spectra of 12 and i rigorously established identity of their stereostructures. Details of X-ray crystallographic study will be reported in a separate paper. (Chemical Equation Presented)
62. A related base-catalyzed epimerization has been reported for the synthesis of 9-epi-mitomycin B, see, Kasai, M.; Kono, M.; Shirahata, K. J. Org. Chem. 1989, 54, 5908.
63. 9a-H in 10, 46, 47, and 48 were found to be 3.1%, 3.2%, 3.3%, and 2.9%, respectively. Based on these results, their stereostructures could be rigorously assigned as depicted. A related assignment of the C-9 stereochemistries has been reported for the structure determination of FR900482(1) (ref. 4).
64. 3·Py), tetra-n-propylammonium perruthenate (TPAP), 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), etc.] gave complicated mixtures of the products probably due to chemical instability of the naked aziridine functionality in 50 and/or 51 under these conditions.
65. It has been reported that the cytotoxicity of FK973 (2) against L1210 murine leukemia cells is ca. 10 time more potent than that of FR900482 (1), see, Masuda, K.; Suzuki, A.; Nakamura, T.; Takagi, S.; Noda, K.; Shinomura, K.; Noguchi, H.; Shibayama, F. Japan, J., Pharmacol. 1989, 51, 219.
66. Studies on alkylation and cross-linking reaction of DNA by natural mitomycin C (3) and unnatural ent-mitomycin C (ent-3) have been reported, see, Gargiulo, D.; Musser, S. S.; Yang, L.; Fukuyama, T.; Tomasz, M. J. Am. Chem. Soc. 1995, 117, 9388.