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Volumn 12, Issue 6, 2010, Pages 1244-1247

A tandem prins/schmidt reaction approach to marine alkaloids: Formal and total syntheses of lepadiformines A and C

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; LEPADIFORMINE; POTASSIUM CHANNEL BLOCKING AGENT;

EID: 77949820579     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100113r     Document Type: Article
Times cited : (58)

References (34)
  • 6
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    • For recent reviews on cylindricine and lepadiformine syntheses(a)
    • For recent reviews on cylindricine and lepadiformine syntheses, see: (a) Weinreb, S. M. Chem. Rev. 2006, 106, 2531-2549.
    • (2006) Chem. Rev. , vol.106 , pp. 2531-2549
    • Weinreb, S.M.1
  • 8
    • 27744521817 scopus 로고    scopus 로고
    • For recent approaches and syntheses of these molecules not covered in the reviews
    • (c) Kibayashi, C. Chem. Pharm. Bull. 2005, 53, 1375-1386. For recent approaches and syntheses of these molecules not covered in the reviews, see:
    • (2005) Chem. Pharm. Bull. , vol.53 , pp. 1375-1386
    • Kibayashi, C.1
  • 22
    • 78650443853 scopus 로고    scopus 로고
    • For a recent review of the intramolecular Schmidt reaction (a) Bräse, S., Banert, K., Eds.; John Wiley and Sons: Chichester, UK
    • For a recent review of the intramolecular Schmidt reaction, see: (a) Grecian, S.; Aubé, J. In Organic Azides: Syntheses and. Applications; Bräse, S., Banert, K., Eds.; John Wiley and Sons: Chichester, UK, 2009; pp 191-237.
    • (2009) In Organic Azides: Syntheses And. Applications , pp. 191-237
    • Grecian, S.1    Aubé, J.2
  • 23
    • 0242628713 scopus 로고    scopus 로고
    • For selected examples of domino reactions involving alkyl azides and Lewis acids (b)
    • For selected examples of domino reactions involving alkyl azides and Lewis acids, see: (b) Reddy, D. S.; Judd, W. R.; Aube J. Org. Lett. 2003, 5, 3899-3902.
    • (2003) Org. Lett. , vol.5 , pp. 3899-3902
    • Reddy, D.S.1    Judd, W.R.2    Aube, J.3
  • 31
    • 84886199418 scopus 로고
    • A related but stepwise spiroannulation/Schmidt sequence was reported previously
    • A related but stepwise spiroannulation/Schmidt sequence was reported previously: Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965-8966.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8965-8966
    • Aubé, J.1    Milligan, G.L.2
  • 32
    • 33845240745 scopus 로고    scopus 로고
    • For a mechanistically related semipinacol arrangement coupled with an intramolecular Schmidt reaction (b)
    • For a mechanistically related semipinacol arrangement coupled with an intramolecular Schmidt reaction, see: (b) Gu, P.; Zhao, Y.-M.; Tu, Y. Q.; Ma, Y.; Zhang, F. Org. Lett. 2006, 8, 5271-5273.
    • (2006) Org. Lett. , vol.8 , pp. 5271-5273
    • Gu, P.1    Zhao, Y.-M.2    Tu, Y.Q.3    Ma, Y.4    Zhang, F.5
  • 33
    • 77949788146 scopus 로고    scopus 로고
    • Initial attempts to remove the methyl group on compounds like 8a led to complex mixtures that included products arising from hydride shifts and elimination
    • Initial attempts to remove the methyl group on compounds like 8a led to complex mixtures that included products arising from hydride shifts and elimination.


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