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Volumn 43, Issue 22, 2004, Pages 2930-2933

A concise asymmetric synthesis of the marine hepatotoxin 7-epicylindrospermopsin

Author keywords

Alkaloids; Cyanobacteria; Cycloaddition; Guanidine; Nitroaldol reaction

Indexed keywords

REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 4544376451     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200454208     Document Type: Article
Times cited : (38)

References (48)
  • 14
    • 4544229524 scopus 로고    scopus 로고
    • http://ntp-server.niehs.nih.gov/htdocs/Results_status/ResstatC/M000072. html
    • For more information, see: http://www.epa.gov/safewater/standard/ucmr/, 2001 and http://ntp-server.niehs.nih.gov/htdocs/Results_status/ResstatC/M000072. html, 2004.
    • (2001)
  • 30
    • 4544357662 scopus 로고    scopus 로고
    • note
    • c) lactone 10 and its enantiomer are available from Aldrich Chemical Co.: catalogue numbers C33,184-8 (10) and C33,181-3 (enantiomer of 10);
  • 41
    • 0000925803 scopus 로고
    • collect.
    • H. Meeiwein, Org. Synth. 1973, collect. vol. 5, 1080.
    • (1973) Org. Synth. , vol.5 , pp. 1080
    • Meeiwein, H.1
  • 42
    • 0035804426 scopus 로고    scopus 로고
    • For a recent review of the Henry reaction, see: F. A. Luzzio, Tetrahedron 2001, 57, 915.
    • (2001) Tetrahedron , vol.57 , pp. 915
    • Luzzio, F.A.1
  • 43
    • 4544365791 scopus 로고    scopus 로고
    • note
    • Treatment with alkoxide bases in THF or DMSO mainly led to ≈ 1:1:1:1 mixtures of all C7/C8 diastereomers. The use of Lewis acids, such as Zn, Mg, or Cu salts, retards the condensation of 15.
  • 45
    • 0030032947 scopus 로고    scopus 로고
    • Contrary to previously reported results (S. Hanessian, P. V. Devasthale, Tetrahedron Lett. 1996, 37, 987), the use of 2 equivalents of TBAF gave the highest selectivity. The use of 0.5 equivalents of TBAF led to a 10:9:7:5 mixture in favor of the anti diastereomer required for the construction of 1, and the use of 1 equivalent of TBAF produced a mixture in which 16 was only slightly favored.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 987
    • Hanessian, S.1    Devasthale, P.V.2
  • 46
    • 4544240759 scopus 로고    scopus 로고
    • note
    • 2O).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.