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Volumn 44, Issue 25, 2005, Pages 3892-3895

Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B

Author keywords

Alkaloids; Natural products; Stephacidin; Total synthesis

Indexed keywords

MOLECULAR ORIENTATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 21244442370     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500655     Document Type: Article
Times cited : (91)

References (25)
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    • c) Isolation of avrainvillamide from a marine fungus off the coast of the Bahamas: W. Fenical, P. R. Jensen, X. C. Cheng, U.S. Patent 6,066,635, 2000 [Chem. Abstr. 2000, 132, 346709];
    • (2000) Chem. Abstr. , vol.132 , pp. 346709
    • Fenical, W.1    Jensen, P.R.2    Cheng, X.C.3
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  • 9
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    • For studies towards the total synthesis of the stephacidins or avrainvillamide, see: A. G. Myers, S. B. Herzon, J. Am. Chem. Soc. 2003, 125, 12080-12081;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12080-12081
    • Myers, A.G.1    Herzon, S.B.2
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    • While this manuscript was under review, beautiful total syntheses of (-)-avrainvillamide and (+)-stephacidin B were reported: S. B. Herzon, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 5342-5344.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5342-5344
    • Herzon, S.B.1    Myers, A.G.2
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    • Bristol-Meyers-Squibb, personal communication
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    • Proline 6 was synthesized by hydroboration, oxidation, esterification, and deprotection of the corresponding Cbz-protected enantiopure allylated proline, see: D. Seebach, M. Boes, R. Naef, W. B. Schweizer, J. Am. Chem. Soc. 1983, 105, 5390-5398;
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    • Seebach, D.1    Boes, M.2    Naef, R.3    Schweizer, W.B.4
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    • PhD Thesis, University of Göttingen
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    • For extensive reviews, see: M. Somei, Heterocycles 1999, 50, 1157-1211;
    • (1999) Heterocycles , vol.50 , pp. 1157-1211
    • Somei, M.1
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    • note
    • Detailed experimental procedures and copies of all spectral data for 15, (+)-1, (+)-3, and (-)-2 are available in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.