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Volumn 34, Issue 7, 2005, Pages 1062-1063

Synthetic study toward antitumour natural product pericosine A

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Indexed keywords


EID: 26044483854     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1062     Document Type: Article
Times cited : (28)

References (23)
  • 16
    • 26044460689 scopus 로고    scopus 로고
    • note
    • 3OD) δ 1.81 (1H, dd, J = 13.5, 11.7 Hz, H-2β), 2.19 (1H, dd, J = 13.5, 5.0 Hz, H-2α), 3.45 (1H, dd, J = 9.6, 3.0 Hz, H-4), 3.78 (3H, s, COOMe), 3.98 (1H, ddd, J = 11.7, 9.6, 5.0 Hz, H-3), 4.10 (1H, dd, J = 3.0, 2.8 Hz, H-5), 4.49 (1H, d, J = 2.8 Hz, H-6). Observation of the NOESY cross peaks H-6/H-4, H-6/H-2β, and H-4/H-2β in 19 supported the conformation shown below. These results elucidated the stereochemistry of C-6 in 5 or C-5 in 6. (Chemical Equation Presented) 6 19 Figure 2.
  • 18
    • 26044447558 scopus 로고    scopus 로고
    • note
    • Observing the NOESY cross peaks H-6/H-4, H-6/H-2β, and H-4/H-2β in 10 as in 19 suggested the configuration at C-4 as shown in Scheme 1.
  • 20
    • 26044444265 scopus 로고    scopus 로고
    • note
    • Observation of the NOESY cross peak between H-4 and H-6 in 13 suggested that H-4 and H-6 had the cis-configuration. And as described in text part, observation of the cross peaks between the proton signal of one of acetonide-methyl groups and H-4 or H-5 in the NOESY spectra of 15, which was derived from 13 via 1, implied that H-4 and H-5 had cis-configuration in 13. Therefore the possibility of epimerization at C-4 or C-6 during transformation from 12 to 13 was denied.
  • 22
    • 26044456612 scopus 로고    scopus 로고
    • note
    • +, 223.0372; Found, 223.0360.
  • 23
    • 26044445103 scopus 로고    scopus 로고
    • note
    • +, 223.0372; Found, 223.0379.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.