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Volumn 10, Issue 3, 2012, Pages 614-622

Synthesis of manzacidin A and C: Efficient construction of quaternary carbon stereocenters bearing nitrogen substituents

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL AMINE; EFFICIENT CONSTRUCTION; MARINE ALKALOIDS; QUATERNARY CARBON; STEREOSELECTIVE CONSTRUCTION; SYNTHETIC METHODS;

EID: 84055200509     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob06559a     Document Type: Article
Times cited : (29)

References (38)
  • 29
    • 0001548880 scopus 로고
    • Method A was successively employed in our synthetic studies of (+)-geranyllinaloisocyanide. See the reference
    • W. J. Bailey J. R. Griffith J. Org. Chem. 1978 43 2690
    • (1978) J. Org. Chem. , vol.43 , pp. 2690
    • Bailey, W.J.1    Griffith, J.R.2
  • 31
    • 85087539289 scopus 로고
    • Titanium tetra-t-butoxide is reported to serve as a catalyst for addition of alcohols to hindered isocyanates. See the reference
    • A. Benali O. Roby B. Carboni M. Vaultier Synthesis 1991 787
    • (1991) Synthesis , pp. 787
    • Benali, A.1    Roby, O.2    Carboni, B.3    Vaultier, M.4
  • 34
    • 0032481423 scopus 로고    scopus 로고
    • Our first approaches to manzacidins involved hydrogenation of enamides such as i. Shortly after we examined this process, Ohfune and Shinada reported a similar reaction using Burk's catalyst. 6j As a result, we abandoned our first plan and explored a new approach for hydrogenation of dienamides.
    • M. J. Burk J. G. Allen W. F. Kiesman J. Am. Chem. Soc. 1998 120 657
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 657
    • Burk, M.J.1    Allen, J.G.2    Kiesman, W.F.3
  • 38
    • 33845551642 scopus 로고
    • 1H NMR analysis of the product 4 showed that no signals corresponding to those of 24 were presented, which confirmed that the α-stereocenter in the α-amino acid ester 7 did not epimerize in the conversion of 7 to 4.
    • D. L. Flynm R. E. Zelle P. A. Grieco J. Org. Chem. 1983 48 2424
    • (1983) J. Org. Chem. , vol.48 , pp. 2424
    • Flynm, D.L.1    Zelle, R.E.2    Grieco, P.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.