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Synfacts 2008(8): 0782-0782
DOI: 10.1055/s-2008-1078529
DOI: 10.1055/s-2008-1078529
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Pinnatoxin A
Contributor(s):Philip Kocienski, Arndt W. SchmidtC. E. Stivala, A. Zakarian*
Florida State University, Tallahassee, USA
Total Synthesis of (+)-Pinnatoxin A
J. Am. Chem. Soc. 2008, 130: 3774-3776
Florida State University, Tallahassee, USA
Total Synthesis of (+)-Pinnatoxin A
J. Am. Chem. Soc. 2008, 130: 3774-3776
Further Information
Publication History
Publication Date:
23 July 2008 (online)
Key words
pinnatoxin A - Ireland-Claisen rearrangement - asymmetric 1,2-addition - spiroacetals - macrocycles
Significance
(+)-Pinnatoxin A is a neurotoxin found in the Pinna shellfish species, presumably acting as a calcium-channel activator. The present study concentrates on a new approach towards ring G using an Ireland-Claisen rearrangement to establish the C5 and C31 stereogenic centers.
Comment
A was synthesized from d-ribose. Deprotonation of E using chiral amide F followed by treatment with TMSCl furnished silylketene acetal G which underwent stereoselective [3,3]-sigmatropic rearrangement upon warming to room temperature.