메뉴 건너뛰기




Volumn 72, Issue 11, 2007, Pages 4284-4287

Acid-catalyzed Aza-Diels-Alder reactions for the total synthesis of (±)-lapatin B

Author keywords

[No Author keywords available]

Indexed keywords

MICROFUNGAL ALKALOIDS; SYNTHETIC ROUTES;

EID: 34249799049     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0705162     Document Type: Article
Times cited : (27)

References (29)
  • 5
    • 33748602640 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see: Mhaske, S. B.; Argade, N. O. Tetrahedron 2006, 62, 9787-9826.
    • (2006) Tetrahedron , vol.62 , pp. 9787-9826
    • Mhaske, S.B.1    Argade, N.O.2
  • 6
    • 0003153862 scopus 로고    scopus 로고
    • For total syntheses of this class of quinazolines, see: a
    • For total syntheses of this class of quinazolines, see: (a) He, F.; Snider, B. B. Synlett 1997, 483-484.
    • (1997) Synlett , pp. 483-484
    • He, F.1    Snider, B.B.2
  • 16
    • 22644439543 scopus 로고    scopus 로고
    • (-)-Lapatin B was isolated from the microfungus Penicillium lapataye: Larsen, T. O.; Petersen, B. O.; Duus, J. O.; Sorensen, D.; Frisvad, J. C.; Hansen, M. E. J. Nat. Prod. 2005, 68, 871-874.
    • (-)-Lapatin B was isolated from the microfungus Penicillium lapataye: Larsen, T. O.; Petersen, B. O.; Duus, J. O.; Sorensen, D.; Frisvad, J. C.; Hansen, M. E. J. Nat. Prod. 2005, 68, 871-874.
  • 20
    • 34249790448 scopus 로고    scopus 로고
    • The modest yield obtained for the unsubstituted azadiene 8 may be due to its lower stability compared to 7 and 9.
    • The modest yield obtained for the unsubstituted azadiene 8 may be due to its lower stability compared to 7 and 9.
  • 21
    • 34249826803 scopus 로고    scopus 로고
    • When a sample of endo cycloadduct 17 was refluxed in dichlorobenzene for 2 days, no conversion to the exo product 16 was observed. The same result was obtained in chloroform in the presence of methyleneoxindole 6.
    • When a sample of endo cycloadduct 17 was refluxed in dichlorobenzene for 2 days, no conversion to the exo product 16 was observed. The same result was obtained in chloroform in the presence of methyleneoxindole 6.
  • 23
    • 34249826508 scopus 로고    scopus 로고
    • B3LYP/6-31+G(d,p)//B3LYP/6-31G(d) energies with PCM solvent corrections. See the Supporting Information
    • B3LYP/6-31+G(d,p)//B3LYP/6-31G(d) energies with PCM solvent corrections. See the Supporting Information.
  • 24
    • 0033599520 scopus 로고    scopus 로고
    • and references cited therein
    • (a) Jnoff, E.; Ghosez, L. J. Am. Chem. Soc. 1999, 121, 2617-2618 and references cited therein,
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 2617-2618
    • Jnoff, E.1    Ghosez, L.2
  • 26
    • 0036625262 scopus 로고    scopus 로고
    • Both lanthanide triflates are known to induce similar selectivities in Diels-Alder reactions: Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227-2302.
    • Both lanthanide triflates are known to induce similar selectivities in Diels-Alder reactions: Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227-2302.
  • 27
    • 34249781878 scopus 로고    scopus 로고
    • One equivalent of diene 9 was reacted with 1.2 equiv of 6 in chloroform overnight at room temperature.
    • One equivalent of diene 9 was reacted with 1.2 equiv of 6 in chloroform overnight at room temperature.
  • 28
    • 34249788046 scopus 로고    scopus 로고
    • In both cases, the selectivity was superior to 98:2. Hydrolysis of 16-19 in the presence of 1 equiv of aqueous 2 N HCl in ethyl acetate afforded the corresponding amides, see the Supporting Information.
    • In both cases, the selectivity was superior to 98:2. Hydrolysis of 16-19 in the presence of 1 equiv of aqueous 2 N HCl in ethyl acetate afforded the corresponding amides, see the Supporting Information.
  • 29
    • 34249797449 scopus 로고    scopus 로고
    • This phenomenon was not observed in the hydrolyses of 16 and 18
    • This phenomenon was not observed in the hydrolyses of 16 and 18.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.