메뉴 건너뛰기




Volumn 68, Issue 2, 2003, Pages 545-563

Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A

Author keywords

[No Author keywords available]

Indexed keywords

STEREOISOMERS;

EID: 0037462345     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0264980     Document Type: Article
Times cited : (72)

References (50)
  • 16
    • 0034649730 scopus 로고    scopus 로고
    • For preliminary communications on portions of this work see: (a) Snider, B. B.; Zeng, H. Org. Lett. 2000, 2, 4103-4106. (b) Snider, B. B.; Zeng, H. Org. Lett. 2002, 4, 1087-1090.
    • (2000) Org. Lett. , vol.2 , pp. 4103-4106
    • Snider, B.B.1    Zeng, H.2
  • 17
    • 0037018453 scopus 로고    scopus 로고
    • For preliminary communications on portions of this work see: (a) Snider, B. B.; Zeng, H. Org. Lett. 2000, 2, 4103-4106. (b) Snider, B. B.; Zeng, H. Org. Lett. 2002, 4, 1087-1090.
    • (2002) Org. Lett. , vol.4 , pp. 1087-1090
    • Snider, B.B.1    Zeng, H.2
  • 32
    • 12244304174 scopus 로고    scopus 로고
    • note
    • 1,3 strain with the carbonyl group. In fumiquinazoline A (1), the methyl group at C-3, which is trans to R, is equatorial-like. Therefore, there is a 81° torsion angle between the axial-like H-3 and N-H (PCMODEL 7.5), which is consistent with the observed 0.3-Hz coupling constant. In fumiquinazoline B (2), the methyl group, which is cis to R, is axial-like. Therefore there is a 46° torsion angle between the equatorial H-3 and N-H, which is consistent with the observed 4.9-Hz coupling constant. The coupling constant reported for 5 in ref 1 is 0.3 Hz, which indicates that the substituents are trans not cis and that this compound actually has structure 6 (50b). The coupling constant reported for 6 in ref 1 is 4.2 Hz, which indicates that the substituents are cis not trans and that this compound actually has structure 5 (50a).
  • 34
    • 12244279020 scopus 로고    scopus 로고
    • note
    • 2 or DDQ was unsuccessful.
  • 41
    • 12244311188 scopus 로고    scopus 로고
    • note
    • 3CN without acetic acid for 2 h yields 54b in 33% yield with 15% of the C-14 epimer, 7% of 60, and 4% of the cyclic ether from the C-14 epimer.
  • 42
    • 12244257517 scopus 로고    scopus 로고
    • note
    • 22 Presumably the selective formation of 59 from 54b is a result of axial-like addition of methanol to the intermediate cation.
  • 48
    • 12244266468 scopus 로고
    • U.S. Patent 3609140, 1971
    • Griot, R. G. U.S. Patent 3609140, 1971; Chem. Abstr. 1971, 75, 151845d.
    • (1971) Chem. Abstr. , vol.75
    • Griot, R.G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.