Literature DB >> 19138148

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

Bruce H Lipshutz1, Benjamin Amorelli.   

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.

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Year:  2009        PMID： 19138148      PMCID： PMC3365511          DOI： 10.1021/ja809542r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

Review 1.  Coenzyme Q10 in health and disease.

Authors:  K Overvad; B Diamant; L Holm; G Holmer; S A Mortensen; S Stender
Journal:  Eur J Clin Nutr       Date:  1999-10       Impact factor: 4.016

2.  STRUCTURE OF PIERCIDIN A.

Authors:  N TAKAHASHI; A SUZUKI; S TAMURA
Journal:  J Am Chem Soc       Date:  1965-05-05       Impact factor: 15.419

3.  An improved synthesis of the "miracle nutrient" coenzyme Q10.

Authors:  Bruce H Lipshutz; Asher Lower; Volker Berl; Karin Schein; Frank Wetterich
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

4.  Total synthesis of piericidin A1 and B1 and key analogues.

Authors:  Martin J Schnermann; F Anthony Romero; Inkyu Hwang; Eiko Nakamaru-Ogiso; Takao Yagi; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

5.  Three classes of inhibitors share a common binding domain in mitochondrial complex I (NADH:ubiquinone oxidoreductase).

Authors:  J G Okun; P Lümmen; U Brandt
Journal:  J Biol Chem       Date:  1999-01-29       Impact factor: 5.157

6.  A convenient and genuine equivalent to HZrCp2Cl generated in situ from ZrCp2Cl2-DIBAL-H.

Authors:  Zhihong Huang; Ei-ichi Negishi
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

7.  Total synthesis of piericidin A1 and B1.

Authors:  Martin J Schnermann; Dale L Boger
Journal:  J Am Chem Soc       Date:  2005-11-16       Impact factor: 15.419

8.  The potential of coenzyme Q 10 (NSC-140865) in cancer treatment.

Authors:  K Folkers
Journal:  Cancer Chemother Rep 2       Date:  1974-12

9.  Titanium(II)-mediated cyclizations of (silyloxy)enynes: a total synthesis of (-)-7-demethylpiericidin A1.

Authors:  Katie A Keaton; Andrew J Phillips
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

10.  Remote asymmetric induction with vinylketene silyl n,o-acetal.

Authors:  Shin-Ichi Shirokawa; Masato Kamiyama; Tomoaki Nakamura; Masakazu Okada; Atsuo Nakazaki; Seijiro Hosokawa; Susumu Kobayashi
Journal:  J Am Chem Soc       Date:  2004-10-27       Impact factor: 15.419
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  9 in total

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Authors:  Wufeng Tang; Shuang Liu; David Degen; Richard H Ebright; Evgeny V Prusov
Journal:  Chemistry       Date:  2014-08-11       Impact factor: 5.236

2.  N-Heterocyclic Carbene Bound Nickel(I) Complexes and Their Roles in Catalysis.

Authors:  Kainan Zhang; Martin Conda-Sheridan; Shayna Cooke; Janis Louie
Journal:  Organometallics       Date:  2011-05-09       Impact factor: 3.876

Review 3.  Negishi coupling: an easy progress for C-C bond construction in total synthesis.

Authors:  Majid M Heravi; Elaheh Hashemi; Niousha Nazari
Journal:  Mol Divers       Date:  2014-03-07       Impact factor: 2.943

Review 4.  The unique chemistry and biology of the piericidins.

Authors:  Xuefeng Zhou; William Fenical
Journal:  J Antibiot (Tokyo)       Date:  2016-06-15       Impact factor: 2.649

5.  Diversity-oriented functionalization of 2-pyridones and uracils.

Authors:  Yong Shang; Chenggui Wu; Qianwen Gao; Chang Liu; Lisha Li; Xinping Zhang; Hong-Gang Cheng; Shanshan Liu; Qianghui Zhou
Journal:  Nat Commun       Date:  2021-05-20       Impact factor: 14.919

6.  Development and Investigation of a Site Selective Palladium-Catalyzed 1,4-Difunctionalization of Isoprene using Pyridine-Oxazoline Ligands.

Authors:  Matthew S McCammant; Matthew S Sigman
Journal:  Chem Sci       Date:  2015-02       Impact factor: 9.825

7.  Total Synthesis of Mycinolide IV and Path-Scouting for Aldgamycin N.

Authors:  Bart Herlé; Georg Späth; Lucas Schreyer; Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-26       Impact factor: 15.336

8.  Cytotoxic Minor Piericidin Derivatives from the Actinomycete Strain Streptomyces psammoticus SCSIO NS126.

Authors:  Kunlong Li; Ziqi Su; Yongli Gao; Xiuping Lin; Xiaoyan Pang; Bin Yang; Huaming Tao; Xiaowei Luo; Yonghong Liu; Xuefeng Zhou
Journal:  Mar Drugs       Date:  2021-07-28       Impact factor: 5.118

Review 9.  Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Authors:  Christopher S Horbaczewskyj; Ian J S Fairlamb
Journal:  Org Process Res Dev       Date:  2022-07-11       Impact factor: 3.858
  9 in total

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