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Synfacts 2011(10): 1125-1125
DOI: 10.1055/s-0030-1261119
DOI: 10.1055/s-0030-1261119
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Collective, Organocatalytic Syntheses of Natural Products: Strychnos Alkaloids
S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan*
Princeton University, USA
Further Information
Publication History
Publication Date:
20 September 2011 (online)
Significance
The MacMillan group reports the highly efficient total syntheses of six members of the Strychnos alkaloids family. The catalytic enantioselective [4+2] cycloaddition of 1 and 2 and subsequent β-elimination-amine conjugate addition sequence provides the common intermediate 4 with excellent yield and enantioselectivity by using secondary amine-Brønsted acid complex 3˙HX as catalyst. Notably, the described asymmetric syntheses need a total of 34 steps from the commercially available starting material for the six natural products.