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Volumn 65, Issue 4, 2000, Pages 1037-1049

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; TRUNKAMIDE A; UNCLASSIFIED DRUG;

EID: 0034712229     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9914566     Document Type: Article
Times cited : (100)

References (54)
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    • For other reverse-prenylated peptide derivatives from the marine environment, see: (a) Nagatsu, A.; Kajitani, H.; Sakakibara, J. Tetrahedron Lett. 1995, 36, 4097. (b) Carroll, A. R.; Feng, Y.; Bowden, B. F.; Coll, J. C. J. Org. Chem. 1996, 61, 4059.
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    • For recent total syntheses, see: (a) Downing, S. V.; Aguilar, E.; Meyers, A. I. J. Org. Chem. 1999, 64, 826. (b) Freeman, D. J.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3251. (c) Norley, M. C.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3087. (d) Moody, C. J.; Bagley, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 601. (e) Kigoshi, H.; Yamada, S. Tetrahedron 1999, 55, 12301.
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    • For recent total syntheses, see: (a) Downing, S. V.; Aguilar, E.; Meyers, A. I. J. Org. Chem. 1999, 64, 826. (b) Freeman, D. J.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3251. (c) Norley, M. C.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3087. (d) Moody, C. J.; Bagley, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 601. (e) Kigoshi, H.; Yamada, S. Tetrahedron 1999, 55, 12301.
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    • For recent total syntheses, see: (a) Downing, S. V.; Aguilar, E.; Meyers, A. I. J. Org. Chem. 1999, 64, 826. (b) Freeman, D. J.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3251. (c) Norley, M. C.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3087. (d) Moody, C. J.; Bagley, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 601. (e) Kigoshi, H.; Yamada, S. Tetrahedron 1999, 55, 12301.
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    • For recent total syntheses, see: (a) Downing, S. V.; Aguilar, E.; Meyers, A. I. J. Org. Chem. 1999, 64, 826. (b) Freeman, D. J.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3251. (c) Norley, M. C.; Pattenden, G. Tetrahedron Lett. 1998, 39, 3087. (d) Moody, C. J.; Bagley, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 601. (e) Kigoshi, H.; Yamada, S. Tetrahedron 1999, 55, 12301.
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    • For a preliminary account of our work, see: Wipf, P.; Uto, Y. Tetrahedron Lett. 1999, 40, 5165. Note added in proof: For a synthesis of mollamide, see: McKeever, B.; Pattenden, G. Tetrahedron Lett. 1999, 40, 9317.
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    • For a preliminary account of our work, see: Wipf, P.; Uto, Y. Tetrahedron Lett. 1999, 40, 5165. Note added in proof: For a synthesis of mollamide, see: McKeever, B.; Pattenden, G. Tetrahedron Lett. 1999, 40, 9317.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 9317
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    • note
    • 3
  • 38
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    • note
    • An N- to C-terminal chain extension sequence was chosen for the preparation of segment 14 rather than the commonly used C- to N-terminus strategy, since removal of the N-Fmoc protective group from dipeptide Fmoc-Phe-Ser(OTBS)-OBn led to diketopiperazine formation.
  • 48
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    • personal communication
    • 3); there were also minor adjustments necessary for NMR spectral data (see Table 1). Prof. B. F. Bowden, personal communication.
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  • 49
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    • 25 We used an alternative sequence of additions following a protocol by Pettit, G. R.; Taylor, S. R. J. Org. Chem. 1996, 61, 2322.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.