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Volumn 71, Issue 7, 2006, Pages 2547-2557

A general, convergent strategy for the construction of indolizidine alkaloids: Total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE ALKALOIDS; SEQUENTIAL CYCLIZATION; TOLUENESULFONYL AZIRIDINES;

EID: 33645515307     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052314g     Document Type: Article
Times cited : (105)

References (87)
  • 6
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    • Paquette, L. A., Ed.; John Wiley & Sons: Chichester
    • (d) Kolb, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; Vol. 5, p 2983.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.5 , pp. 2983
    • Kolb, M.1
  • 24
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    • For early examples of N-Ts aziridine ring opening reactions by lithiated dithiane anions, see: (a) Bates, G. S. J. Chem. Soc. Chem. Commun. 1979, 161.
    • (1979) J. Chem. Soc. Chem. Commun. , pp. 161
    • Bates, G.S.1
  • 28
    • 0035074681 scopus 로고    scopus 로고
    • Prior to the work reported here, there was one report of an intramolecular linchpin reaction between bis(methylthio)trimethylsilylmethane and 1,4-biselectrophile, 1,2-epimino-3,4-epoxy-(N-Ts)butane, in which the aziridine moiety played the role as the second electrophile: Harms, G.; Schaumann, E.; Adiwidjaja, G. Synthesis 2001, 577.
    • (2001) Synthesis , pp. 577
    • Harms, G.1    Schaumann, E.2    Adiwidjaja, G.3
  • 35
  • 63
    • 33645523681 scopus 로고    scopus 로고
    • note
    • The relative and absolute configurations were confirmed by Kakisawa analysis of the Mosher esters of diol (+)-14; see ref 17.
  • 67
    • 33645525352 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra of synthetic (-)-indolizidine 223AB.
  • 76
    • 0000178458 scopus 로고
    • (b) Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S. Tetrahedron 1990, 46, 3667. Aldehyde (-)-34 was prepared in 4 steps and 95% overall yield from commercially available ethyl (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenoate (i): See Supporting Information for details.
    • (1990) Tetrahedron , vol.46 , pp. 3667
    • Chattopadhyay, S.1    Mamdapur, V.R.2    Chadha, M.S.3
  • 86
    • 33645517724 scopus 로고    scopus 로고
    • note
    • The stereochemistry of (+)-55 was later confirmed by comparison of the NMR data of (-)-41 with those of known (+)-41; see ref 13.
  • 87
    • 33645503362 scopus 로고    scopus 로고
    • note
    • We thank Dr. John W. Daly, National Institutes of Health, for kindly providing the 400 MHz 1H NMR and the proton/carbon HMBC spectra for the natural antipode of alkaloid 205B.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.