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Volumn 10, Issue 23, 2008, Pages 5449-5452

Total synthesis of (-)-amathaspiramide F

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMATHASPIRAMIDE F; PYRROLIDINE DERIVATIVE; SILANE DERIVATIVE; SPIRO COMPOUND;

EID: 61349199532     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802179e     Document Type: Article
Times cited : (32)

References (29)
  • 2
    • 0141518579 scopus 로고    scopus 로고
    • For several biologically active natural products containing cyclic spirolactam or hemiaminal structure, see the following examples. Massadine: (a) Nishimura, S, Matsunaga, S, Shibazaki, M, Suzuki, K, Furihata, K, van Soest, R. W. M, Fusetani, N Org. Lett. 2003, 5, 2255-2257
    • For several biologically active natural products containing cyclic spirolactam or hemiaminal structure, see the following examples. Massadine: (a) Nishimura, S.; Matsunaga, S.; Shibazaki, M.; Suzuki, K.; Furihata, K.; van Soest, R. W. M.; Fusetani, N Org. Lett. 2003, 5, 2255-2257.
  • 4
    • 0033524887 scopus 로고    scopus 로고
    • Axinellamine: (c) Urban, S.; Leone, P. A.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hopper, J. N. A.; Quinn, R. J. J. Org. Chem. 1999, 64, 731-735.
    • Axinellamine: (c) Urban, S.; Leone, P. A.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hopper, J. N. A.; Quinn, R. J. J. Org. Chem. 1999, 64, 731-735.
  • 5
    • 61349114114 scopus 로고    scopus 로고
    • Pseurotin A: (d) Komagata, D.; Fujita, S.; Yamashita, N.; Saito, S.; Morino, T. J. Antibiot. 1996, 49, 958-959.
    • Pseurotin A: (d) Komagata, D.; Fujita, S.; Yamashita, N.; Saito, S.; Morino, T. J. Antibiot. 1996, 49, 958-959.
  • 15
    • 33748826144 scopus 로고
    • 2-assisted dianionic enolate Claisen rearrangement of the N-protected α-amino acid allyl ester was originally developed by Kazmaier: Kazmaier, U
    • 2-assisted dianionic enolate Claisen rearrangement of the N-protected α-amino acid allyl ester was originally developed by Kazmaier: Kazmaier, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 998-999.
    • (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 998-999
  • 19
    • 61349123432 scopus 로고    scopus 로고
    • Hydrogenation of 3 using the Lindlar catalyst did not give any olefin product even at high pressure (5 atm). The use of Pd/C produced the corresponding alkane.
    • Hydrogenation of 3 using the Lindlar catalyst did not give any olefin product even at high pressure (5 atm). The use of Pd/C produced the corresponding alkane.
  • 20
    • 61349198051 scopus 로고    scopus 로고
    • The absolute configuration of the minor isomer was not determined
    • The absolute configuration of the minor isomer was not determined.
  • 21
    • 61349130553 scopus 로고    scopus 로고
    • 2 resulted in the decreased yield of 7 28
    • 2 resulted in the decreased yield of 7 (28%).
  • 22
    • 0003034713 scopus 로고    scopus 로고
    • It is reported that the ozonolysis of the vinylsilane does not give the corresponding aldehyde; see: (a) Büchi, G, Wüest, H. J. Am. Chem. Soc. 1978, 100, 294-295
    • It is reported that the ozonolysis of the vinylsilane does not give the corresponding aldehyde; see: (a) Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1978, 100, 294-295.
  • 24
    • 61349128320 scopus 로고    scopus 로고
    • The spirolactone 13 was obtained as a single diastereomer. The relative stereochemistry of 13 was not determined.
    • The spirolactone 13 was obtained as a single diastereomer. The relative stereochemistry of 13 was not determined.
  • 25
    • 61349183629 scopus 로고    scopus 로고
    • Lower amounts of methylamine (2 equiv) resulted in the decreased yield of 12 (<20%).
    • Lower amounts of methylamine (2 equiv) resulted in the decreased yield of 12 (<20%).
  • 26
    • 0037131653 scopus 로고    scopus 로고
    • Electrophilic 4,6-dibromination of 3-substituted phenol: (a) Osuna, M. R.; Agurrie, G.; Somanathan, R.; Molins, E. Tetrahedron: Asymmetry 2002, 13, 2261-2266.
    • Electrophilic 4,6-dibromination of 3-substituted phenol: (a) Osuna, M. R.; Agurrie, G.; Somanathan, R.; Molins, E. Tetrahedron: Asymmetry 2002, 13, 2261-2266.
  • 29
    • 61349177755 scopus 로고    scopus 로고
    • 1
    • 1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.