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Synfacts 2010(8): 0951-0951
DOI: 10.1055/s-0030-1257801
DOI: 10.1055/s-0030-1257801
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
NHC-Catalyzed Desymmetrization in Natural Product Synthesis
E. M. Phillips, J. M. Roberts, K. A. Scheidt*
Northwestern University, Evanston, USA
Further Information
Publication History
Publication Date:
22 July 2010 (online)

Significance
Scheidt and co-workers report the synthesis of three bakkenolide natural products, employing their previously developed carbene-catalyzed desymmetrization of 1,3-diketones (J. Am. Chem. Soc. 2007, 129, 10098) as an early key step. Diketone 2 was cyclized in the presence of the A-derived carbene to give β-lactone 3 in good yield and excellent enantioselectivity. Another interesting aspect is the double-bond isomerization of 5 to 6 prior to the reduction to obtain 7 with an equatorial methyl group. The final steps were adapted from a related work by Greene, Deprés, and co-workers (J. Am. Chem. Soc. 1996, 118, 9992).