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Volumn 4, Issue 15, 2002, Pages 2577-2579

First asymmetric total synthesis of (+)-sparteine

Author keywords

[No Author keywords available]

Indexed keywords

2,5 NORBORNADIENE; 2,5-NORBORNADIENE; CARDIOVASCULAR AGENT; NORBORNANE DERIVATIVE; SPARTEINE;

EID: 0001147659     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026230v     Document Type: Article
Times cited : (124)

References (32)
  • 1
    • 0026726569 scopus 로고
    • Isolation and structure determination
    • Biological activity: (a) Seeger, R.; Neumann, H. G. Inst. Pharmakol. Toxikol. 1992, 132, 1577-1581. Isolation and structure determination:
    • (1992) Inst. Pharmakol. Toxikol. , vol.132 , pp. 1577-1581
    • Seeger, R.1    Neumann, H.G.2
  • 4
    • 0000679903 scopus 로고    scopus 로고
    • A SciFinder search for the words "sparteine" and "synthesis" for the period of 1995-2002 yielded 317 references. For reviews of work in this area, see: (a) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
    • (1996) Acc. Chem. Res. , vol.29 , pp. 552-560
    • Beak, P.1    Basu, A.2    Gallagher, D.J.3    Park, Y.S.4    Thayumanavan, S.5
  • 17
    • 0029964219 scopus 로고    scopus 로고
    • Early studies related to this synthesis have appeared: Wendt, J. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 1531-1534.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1531-1534
    • Wendt, J.A.1    Aubé, J.2
  • 20
    • 84872276707 scopus 로고    scopus 로고
    • note
    • This aldehyde was prepared from butanediol in 90% overall yield by monobenzylation followed by TEMPO oxidation.
  • 23
    • 84872273554 scopus 로고    scopus 로고
    • note
    • 4), but there is no evidence for coordination of the ketone carbonyl in even a very large excess of Lewis acid (> 20 equiv). (2) Even simple acid-promoted reactions such as dimethyl ketal formation of compounds such as 5 have proven difficult.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.