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Volumn 8, Issue 15, 2006, Pages 3275-3278

Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (±)-aspidophytine

Author keywords

[No Author keywords available]

Indexed keywords

ASPIDOPHYTINE; FUSED HETEROCYCLIC RINGS; INDOLE ALKALOID; RHODIUM;

EID: 33746916417     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061137i     Document Type: Article
Times cited : (140)

References (70)
  • 1
    • 29944444144 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego, CA
    • Saxton, J. E. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998; Vol. 51, pp 1-197.
    • (1998) The Alkaloids: Chemistry and Biology , vol.51 , pp. 1-197
    • Saxton, J.E.1
  • 5
    • 0001004640 scopus 로고
    • For the first synthesis of aspidospermine and vindoline, see: (a) Stork, G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2872
    • Stork, G.1    Dolfini, J.E.2
  • 52
    • 26444541805 scopus 로고    scopus 로고
    • and references therein
    • Boger and co-workers have recently described an alternate approach to onium ylides based on a [4+2]-cycloaddition of 1,3,4-oxadiazoles followed by a thermal extrusion of nitrogen and have elegantly exploited this chemistry for the construction of a variety of aspidosperma alkaloid targets. See: Choi, Y.; Ishikawa, H.; Velcicky, J.; Elliott, G. I.; Miller, M. M.; Boger, D. L. Org. Lett. 2005, 7, 4539 and references therein.
    • (2005) Org. Lett. , vol.7 , pp. 4539
    • Choi, Y.1    Ishikawa, H.2    Velcicky, J.3    Elliott, G.I.4    Miller, M.M.5    Boger, D.L.6
  • 63
    • 33746917012 scopus 로고    scopus 로고
    • note
    • 15 the exo cycloadducts 11 and 22 were the exclusive products isolated from the Rh(II)-catalyzed reaction. We assume that the bulky tert-butyl ester functionality blocks the endo approach thereby resulting in cycloaddition taking place from the less-congested exo face.
  • 64
    • 33746885345 scopus 로고    scopus 로고
    • note
    • The authors have deposited coordinates for structure 24 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, B2 1EZ, U.K.
  • 65
    • 85077854948 scopus 로고
    • For a review of dealkoxycarbonylations, see: Krapcho, A. P. Synthesis 1982, 805 and 893.
    • (1982) Synthesis , pp. 805
    • Krapcho, A.P.1
  • 68
    • 33746880898 scopus 로고    scopus 로고
    • note
    • Structure 25 was established on the basis of an X-ray crystal structure analysis. A more detailed study of this unusual rearrangement is currently underway in our laboratory.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.