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Volumn 47, Issue 16, 2006, Pages 2787-2791

Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

Author keywords

Antibiotic; Deconjugative asymmetric sulfenylation; Inhibitor of fatty acid synthase

Indexed keywords

3 DEMETHYL DERIVATIVE; ALDEHYDE; THIOLACTOMYCIN; UNCLASSIFIED DRUG;

EID: 33644977648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.058     Document Type: Article
Times cited : (18)

References (31)
  • 18
    • 0345304282 scopus 로고    scopus 로고
    • Deconjugative asymmetric allylation of a dienolate with formation of a quarternary asymmetric center has been recently reported by Kobayashi et al. T. Abe, T. Suzuki, K. Sekiguchi, S. Hosokawa, and S. Kobayashi Tetrahedron Lett. 44 2003 9303 9305
    • (2003) Tetrahedron Lett. , vol.44 , pp. 9303-9305
    • Abe, T.1    Suzuki, T.2    Sekiguchi, K.3    Hosokawa, S.4    Kobayashi, S.5
  • 20
    • 0036182498 scopus 로고    scopus 로고
    • According to the procedure reported by Fujiki et al., 6 was prepared from 3-bromopropionaldehyde dimethylacetal (i ) as shown below. K. Fujiki, N. Tanifuji, Y. Sakaki, and T. Yokoyama Synthesis 2002 343 348
    • (2002) Synthesis , pp. 343-348
    • Fujiki, K.1    Tanifuji, N.2    Sakaki, Y.3    Yokoyama, T.4
  • 23
    • 33644977345 scopus 로고    scopus 로고
    • note
    • 4p-Me) underwent deconjugative asymmetric α-sulfenylation similar to 1, the methylsulfenyl and the (2-trimethylsilyl)ethylsulfenyl group introduced into the reaction products could not be elaborated to a thiol or an acylsulfenyl group.
  • 24
    • 33644975038 scopus 로고    scopus 로고
    • note
    • R 14.7 min (5), 10.4 min [the (3′Z)-isomer of 5 ], 25.1 min (11 )].
  • 25
    • 33644967653 scopus 로고    scopus 로고
    • note
    • +H): 434.2001. Found 434.1967.
  • 26
    • 33644977586 scopus 로고    scopus 로고
    • note
    • The structure of the (3′Z)-isomer of 5 was determined by NOESY spectrum which was observed between C-3′ H and C-4′ Me.
  • 27
    • 0034641497 scopus 로고    scopus 로고
    • Taking into account its electronic and steric effects, it is anticipated that I can participate in the reaction more preferentially than II. See: S. Hosokawa, K. Sekiguchi, M. Enemoto, and S. Kobayashi Tetrahedron Lett. 41 2000 6429 6433
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6429-6433
    • Hosokawa, S.1    Sekiguchi, K.2    Enemoto, M.3    Kobayashi, S.4
  • 28
    • 33644974645 scopus 로고    scopus 로고
    • note
    • R 11.0 min (1 ), 14.9 min (ent-1 ). Daicel Chiralcel OJ ∅0.46 cm × 25 cm, hexane/EtOH/TFA = 99:1:0.1, flow rate 1.0 mL/min, 17.9 min (2 ) and 22.5 min (ent-2 ) detection at 238 nm).
  • 29
    • 33644973165 scopus 로고    scopus 로고
    • note
    • 20).
  • 31
    • 33644978054 scopus 로고    scopus 로고
    • note
    • Antibacterial activity of 1, ent-1, 2 and ent-2 were 128 μg/mL, >128 μg/mL, >128 μg/mL and >128 μg/mL against S. aureus and 0.25 μg/mL, >128 μg/mL, 16 μg/mL and >128 μg/mL against. M. catarrhalis, respectively. Evaluation of the inhibitory activity of those compounds against FAS is in progress.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.