Decagram-scale synthesis of the neocarzinostatin carboxylic acid

European Journal of Organic Chemistry

Volumn , Issue 14, 2000, Pages 2605-2611

  Görth, Felix Christian ^a   Rucker, Mark ^b   Eckhardt, Matthias ^c   Brückner, Reinhard ^d  

^a BASF SE   (Germany)

^b Sigma Aldrich Produktions GmbH   (Germany)

^c SANOFI   (France)

^d UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Antibiotics; Aromatization; Cyclizations; Heck coupling; Natural products; Neocarzinostatin

Indexed keywords

ACRYLIC ACID ETHYL ESTER; CARBOXYLIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE; ZINOSTATIN;

AROMATIZATION; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037570115     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:14<2605::aid-ejoc2605>3.3.co;2-p     Document Type: Article

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37. Preparation: L.-F. Tietze, H. Meier, E. Voß, Synthesis 1988, 274-277 (1st step); J. Wiguny, H. J. Schäfer, Liebigs Ann. Chem. 1994, 225-233 (steps 2-3).
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40. Similarly, 3-methylveratrol was brominated in separate operations first at the nucleus and then in the benzylic position by M. Albrecht, Synthesis 1996, 230-236.
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46. Procedure: see ref.[9a]
47. D. R. Williams, P. D. Lowder, Y. Gu, D. A. Brooks, Tetrahedron Lett. 1997, 38, 331-334.
48. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem 1978, 43, 2923-2925.
49. Footnote 19 in ref.[5]
50. Footnote 18 in ref.[5]