Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2009 Feb 4;131(4):1396-7.
doi: 10.1021/ja809542r.

Total synthesis of piericidin A1. Application of a modified Negishi carboalumination-nickel-catalyzed cross-coupling

Bruce H Lipshutz  1 , Benjamin Amorelli
Affiliations

Total synthesis of piericidin A1. Application of a modified Negishi carboalumination-nickel-catalyzed cross-coupling

Bruce H Lipshutz et al. J Am Chem Soc. .

Abstract

A total synthesis of the mitochondrial complex I inhibitor piericidin A1 is described. It features a unique strategy for the key disconnection, highlighting a modified Negishi carboalumination/Ni-catalyzed cross-coupling on a polyenyne precursor.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Retrosynthetic Analysis of Piericidin A1
Scheme 2
Scheme 2
Preparation of Chloromethylated Picoline 4
Scheme 3
Scheme 3
Preparation of Alkyne Coupling Partner 18, and Completion of the Synthesis of Piericidin A1
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Takahishi N, Suzuki A, Tamura S. J. Am. Chem. Soc. 1965;87:2066–2068. - PubMed
    1. Overvad K, Diamant B, Holm L, et al. Eur. J. Clin. Nutr. 1999;53:764–770. - PubMed
    1. Folkers K. Cancer Chemother. Rep. 2. 1974;4:19–22. - PubMed
    1. Okun JG, Lummen P, Brandt U. J. Biol. Chem. 1999;274:2625–2630. and references cited therein. - PubMed

    1. The total synthesis of piericidin A1 was reported: Schnermann MJ, Boger DL. J. Am. Chem. Soc. 2005;127:15704–15705. Schnermann MJ, Romero FA, Hwang I, Nakamaru-Ogiso E, Yagi T, Boger DL. J. Am. Chem.Soc. 2006;128:11799–11807.. The total synthesis of 7-demethylpiericidin A1 was reported: Keatin KA, Phillips AJ. J. Am. Chem. Soc. 2006;128:408–409.

Publication types