Literature DB >> 16562900

Total synthesis of enantiopure (+)-gamma-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation.

Bruno D Chapsal1, Iwao Ojima.   

Abstract

[reaction: see text] A highly efficient short total synthesis of (+)-gamma-lycorane (>99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite ligands.

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Year:  2006        PMID： 16562900      PMCID： PMC2562274          DOI： 10.1021/ol060181v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation.

Authors:  Alexandre Alexakis; Damien Polet
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

Review 3.  Amaryllidaceae and Sceletium alkaloids.

Authors:  Zhong Jin
Journal:  Nat Prod Rep       Date:  2005-01-10       Impact factor: 13.423

4.  Kinetic study of various phosphoramidite ligands in the iridium-catalyzed allylic substitution.

Authors:  Damien Polet; Alexandre Alexakis
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

5.  Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-gamma-lycorane.

Authors:  Lin Dong; Yan-Jun Xu; Lin-Feng Cun; Xin Cui; Ai-Qiao Mi; Yao-Zhong Jiang; Liu-Zhu Gong
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

6.  A simple iridium catalyst with a single resolved stereocenter for enantioselective allylic amination. Catalyst selection from mechanistic analysis.

Authors:  Andreas Leitner; Shashank Shekhar; Mark J Pouy; John F Hartwig
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

7.  Bulky monodentate phosphoramidites in palladium-catalyzed allylic alkylation reactions: aspects of regioselectivity and enantioselectivity.

Authors:  Maarten D K Boele; Paul C J Kamer; Martin Lutz; Anthony L Spek; Johannes G de Vries; Piet W N M van Leeuwen; Gino P F van Strijdonck
Journal:  Chemistry       Date:  2004-12-03       Impact factor: 5.236

8.  Asymmetric allylic alkylation, an enabling methodology.

Authors:  Barry M Trost
Journal:  J Org Chem       Date:  2004-09-03       Impact factor: 4.354

9.  Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes.

Authors:  Hojae Choi; Zihao Hua; Iwao Ojima
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

10.  New biphenol-based, fine-tunable monodentate phosphoramidite ligands for catalytic asymmetric transformations.

Authors:  Zihao Hua; Victor C Vassar; Hojae Choi; Iwao Ojima
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-12       Impact factor: 11.205
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  4 in total

1.  Total synthesis of (±)-γ-lycorane via the electrocyclic ring closure of a divinylpyrroline.

Authors:  Raymond J Huntley; Raymond L Funk
Journal:  Tetrahedron Lett       Date:  2011-12-14       Impact factor: 2.415

2.  Desymmetrization of meso-2,5-diallylpyrrolidinyl ureas through asymmetric palladium-catalyzed carboamination: stereocontrolled synthesis of bicyclic ureas.

Authors:  Nicholas R Babij; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-03       Impact factor: 15.336

3.  Hydroamination of Dihapto-Coordinated Benzene and Diene Complexes of Tungsten: Fundamental Studies and the Synthesis of γ-Lycorane.

Authors:  Katy B Wilson; Hannah S Nedzbala; Spenser R Simpson; Megan N Ericson; Karl S Westendorff; Mahendra D Chordia; Diane A Dickie; W Dean Harman
Journal:  Helv Chim Acta       Date:  2021-08-10       Impact factor: 2.164

Review 4.  Applications of Friedel-Crafts reactions in total synthesis of natural products.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Pegah Saedi; Tayebeh Momeni
Journal:  RSC Adv       Date:  2018-12-03       Impact factor: 4.036
  4 in total

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