Literature DB >> 23837485

An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.

Ke Kong1, John A Enquist, Monica E McCallum, Genessa M Smith, Takanori Matsumaru, Elnaz Menhaji-Klotz, John L Wood.   

Abstract

This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

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Year:  2013        PMID: 23837485      PMCID: PMC6775640          DOI: 10.1021/ja405548b

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


  8 in total

1.  An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem Heck/carbonylation strategy.

Authors:  Gerald D Artman; Steven M Weinreb
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

2.  Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.

Authors:  Biao Lu; Chaoqun Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

3.  Absolute stereochemistry of citrinadins a and B from marine-derived fungus.

Authors:  Takao Mugishima; Masashi Tsuda; Yuu Kasai; Haruaki Ishiyama; Eri Fukushi; Jun Kawabata; Masayuki Watanabe; Kenichi Akao; Jun'ichi Kobayashi
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

4.  Concise, stereocontrolled synthesis of the citrinadin B core architecture.

Authors:  Carlos A Guerrero; Erik J Sorensen
Journal:  Org Lett       Date:  2011-09-06       Impact factor: 6.005

5.  Citrinadin A, a novel pentacyclic alkaloid from marine-derived fungus Penicillium citrinum.

Authors:  Masashi Tsuda; Yuu Kasai; Kazusei Komatsu; Teruo Sone; Michiko Tanaka; Yuzuru Mikami; Jun'ichi Kobayashi
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

6.  Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: scope, selectivity, and applications in synthesis.

Authors:  Varinder K Aggarwal; Caroline L Winn
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

7.  Concise, stereoselective approach to the spirooxindole ring system of citrinadin A.

Authors:  Martin Pettersson; Daniel Knueppel; Stephen F Martin
Journal:  Org Lett       Date:  2007-10-06       Impact factor: 6.005

8.  PF1270A, B and C, novel histamine H3 receptor ligands produced by Penicillium waksmanii PF1270.

Authors:  Nobuaki Kushida; Naoko Watanabe; Takako Okuda; Fumikazu Yokoyama; Yasuhiro Gyobu; Takashi Yaguchi
Journal:  J Antibiot (Tokyo)       Date:  2007-11       Impact factor: 2.649

  8 in total
  19 in total

1.  Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles.

Authors:  Olga A Mukhina; Dmitry M Kuznetsov; Teresa M Cowger; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-30       Impact factor: 15.336

2.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

3.  Synthetic studies toward the citrinadin A and B core architecture.

Authors:  Devon A Mundal; Richmond Sarpong
Journal:  Org Lett       Date:  2013-09-19       Impact factor: 6.005

4.  Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

Authors:  Michael Rajesh Stephen; M Toufiqur Rahman; V V N Phani Babu Tiruveedhula; German O Fonseca; Jeffrey R Deschamps; James M Cook
Journal:  Chemistry       Date:  2017-10-18       Impact factor: 5.236

5.  Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy.

Authors:  Eric T Newcomb; Phil C Knutson; Blaine A Pedersen; Eric M Ferreira
Journal:  J Am Chem Soc       Date:  2015-12-30       Impact factor: 15.419

6.  Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group.

Authors:  Qingliang Yang; Jon T Njardarson
Journal:  Tetrahedron Lett       Date:  2013-12-18       Impact factor: 2.415

7.  Discovery and Biocatalytic Application of a PLP-Dependent Amino Acid γ-Substitution Enzyme That Catalyzes C-C Bond Formation.

Authors:  Mengbin Chen; Chun-Ting Liu; Yi Tang
Journal:  J Am Chem Soc       Date:  2020-06-01       Impact factor: 15.419

8.  Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.

Authors:  Adam M Levinson
Journal:  Org Lett       Date:  2014-08-29       Impact factor: 6.005

Review 9.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

10.  Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins.

Authors:  Zhiwen Liu; Fanglong Zhao; Boyang Zhao; Jie Yang; Joseph Ferrara; Banumathi Sankaran; B V Venkataram Prasad; Biki Bapi Kundu; George N Phillips; Yang Gao; Liya Hu; Tong Zhu; Xue Gao
Journal:  Nat Commun       Date:  2021-07-06       Impact factor: 14.919

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