Literature DB >> 20509657

Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.

John D Trzupek1, Dongjoo Lee, Brendan M Crowley, Vasilios M Marathias, Samuel J Danishefsky.   

Abstract

An appropriately constructed 2-substituted derivative of l-tryptophan undergoes conversion to a prephalarine structure in a single step. The reaction occurs in a diastereoselective fashion, leading shortly thereafter to the naturally occurring version of the alkaloid phalarine.

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Year:  2010        PMID： 20509657      PMCID： PMC2895623          DOI： 10.1021/ja1030968

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


  10 in total

1.  Synthesis of the Functionalized Macrocyclic Core of Proteasome Inhibitors TMC-95A and B This work was supported by grants from the National Institutes of Health (grant CA28824). We thank Dr. George Sukenick and Sylvi Rusli of the MSKCC NMR Core Facility for NMR and mass spectral analyses (NIH Grant CA08748).

Authors:  Songnian Lin; Samuel J. Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2001-05-18       Impact factor: 15.336

2.  The total synthesis of proteasome inhibitors TMC-95A and TMC-95B: discovery of a new method to generate cis-propenyl amides.

Authors:  Songnian Lin; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2002-02-01       Impact factor: 15.336

3.  Highly enantioselective catalytic acyl-pictet-spengler reactions.

Authors:  Mark S Taylor; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419

4.  Total synthesis of phalarine.

Authors:  Chaomin Li; Collin Chan; Annekatrin C Heimann; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  On the rearrangement of an azaspiroindolenine to a precursor to phalarine: mechanistic insights.

Authors:  Chaomin Li; Collin Chan; Annekatrin C Heimann; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Catalytic asymmetric Pictet-Spengler reaction.

Authors:  Jayasree Seayad; Abdul Majeed Seayad; Benjamin List
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

7.  Tandem radical decarboxylation-oxidation of amino acids: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping

Authors: 
Journal:  J Org Chem       Date:  2000-08-11       Impact factor: 4.354

8.  Lessons from the Total Synthesis of (±) Phalarine: Insights Into the Mechanism of the Pictet-Spengler Reaction.

Authors:  John D Trzupek; Chaomin Li; Collin Chan; Brendan M Crowley; Annekatrin C Heimann; Samuel J Danishefsky
Journal:  Pure Appl Chem       Date:  2010-04-06       Impact factor: 2.453

9.  Decarboxylative reduction of free aliphatic carboxylic acids by photogenerated cation radical.

Authors:  Yasuharu Yoshimi; Tatsuya Itou; Minoru Hatanaka
Journal:  Chem Commun (Camb)       Date:  2007-10-17       Impact factor: 6.222

Review 10.  Gelsemine: a thought-provoking target for total synthesis.

Authors:  Hong Lin; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-03       Impact factor: 15.336
  10 in total
  5 in total

1.  Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

2.  Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.

Authors:  Fan Liu; Mohammad Movassaghi
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

Review 3.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

Review 4.  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

5.  Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate.

Authors:  Sangki Lee; Jewon Yang; Sehun Yang; Geumwoo Lee; Daehyun Oh; Min Woo Ha; Suckchang Hong; Hyeung-Geun Park
Journal:  Front Chem       Date:  2020-11-12       Impact factor: 5.221
  5 in total

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