Literature DB >> 28706345

A FISCHER INDOLIZATION STRATEGY TOWARD THE TOTAL SYNTHESIS OF (-)-GONIOMITINE.

Beau P Pritchett1, Jun Kikuchi1, Yoshitaka Numajiri1, Brian M Stoltz1.   

Abstract

A Fischer indolization strategy toward the core of (-)-goniomitine is reported. Initial investigations into the Pd-catalyzed asymmetric allylic alkylation of dihydropyrido[1,2-a]indolone (DHPI) substrates are also discussed.

Entities:  

Year:  2017        PMID: 28706345      PMCID: PMC5502790          DOI: 10.3987/COM-16-S(S)80

Source DB:  PubMed          Journal:  Heterocycles        ISSN: 0385-5414            Impact factor:   0.831


  20 in total

1.  Catalytic selective cyclizations of aminocyclopropanes: formal synthesis of aspidospermidine and total synthesis of goniomitine.

Authors:  Filippo De Simone; Jürg Gertsch; Jérôme Waser
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-02       Impact factor: 15.336

2.  Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Authors:  Nolan T McDougal; Jan Streuff; Herschel Mukherjee; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2010-10-20       Impact factor: 2.415

3.  Total Synthesis of (±)-Goniomitine via Radical Translocation.

Authors:  Jessica K Vellucci; Christopher M Beaudry
Journal:  Org Lett       Date:  2015-09-08       Impact factor: 6.005

4.  Palladium-catalyzed decarboxylative vinylation of potassium nitrophenyl acetate: application to the total synthesis of (±)-goniomitine.

Authors:  Zhengren Xu; Qian Wang; Jieping Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-07       Impact factor: 15.336

5.  Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: formal total synthesis of (±)-goniomitine.

Authors:  Bing Zhou; Juanjuan Du; Yaxi Yang; Yuanchao Li
Journal:  Chemistry       Date:  2014-08-21       Impact factor: 5.236

6.  Enantioselective synthesis of α-secondary and α-tertiary piperazin-2-ones and piperazines by catalytic asymmetric allylic alkylation.

Authors:  Katerina M Korch; Christian Eidamshaus; Douglas C Behenna; Sangkil Nam; David Horne; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-07       Impact factor: 15.336

7.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

8.  Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.

Authors:  Nathan B Bennett; Douglas C Duquette; Jimin Kim; Wen-Bo Liu; Alexander N Marziale; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2013-02-27       Impact factor: 5.236

9.  Pd(II)-catalyzed regioselective 2-alkylation of indoles via a norbornene-mediated C-H activation: mechanism and applications.

Authors:  Lei Jiao; Eberhardt Herdtweck; Thorsten Bach
Journal:  J Am Chem Soc       Date:  2012-08-22       Impact factor: 15.419

10.  Enantioselective synthesis of α-quaternary Mannich adducts by palladium-catalyzed allylic alkylation: total synthesis of (+)-sibirinine.

Authors:  Yoshitaka Numajiri; Beau P Pritchett; Koji Chiyoda; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2015-01-20       Impact factor: 15.419

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  3 in total

1.  Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.

Authors:  Beau P Pritchett; Etienne J Donckele; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-05       Impact factor: 15.336

Review 2.  Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.

Authors:  Majid M Heravi; Zahra Amiri; Kosar Kafshdarzadeh; Vahideh Zadsirjan
Journal:  RSC Adv       Date:  2021-10-15       Impact factor: 4.036

3.  Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones.

Authors:  Douglas C Duquette; Alexander Q Cusumano; Louise Lefoulon; Jared T Moore; Brian M Stoltz
Journal:  Org Lett       Date:  2020-06-16       Impact factor: 6.005

  3 in total

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