Literature DB >> 16771478

The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone.

Ryan M McFadden1, Brian M Stoltz.   

Abstract

Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.

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Year:  2006        PMID: 16771478     DOI: 10.1021/ja061853f

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


  34 in total

1.  Construction of Tertiary Chiral Centers by Pd-catalyzed Asymmetric Allylic Alkylation of Prochiral Enolate Equivalents.

Authors:  Yusuke Kita; Yoshitaka Numajiri; Noriko Okamoto; Brian M Stoltz
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

2.  Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine.

Authors:  Arun K Ghosh; Joshua R Born; Luke A Kassekert
Journal:  J Org Chem       Date:  2019-04-02       Impact factor: 4.354

Review 3.  Enantioselective Tsuji allylations.

Authors:  Justin T Mohr; Brian M Stoltz
Journal:  Chem Asian J       Date:  2007-12-03

4.  The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.

Authors:  John A Enquist; Brian M Stoltz
Journal:  Nature       Date:  2008-06-26       Impact factor: 49.962

Review 5.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

Review 6.  Protecting-group-free synthesis as an opportunity for invention.

Authors:  Ian S Young; Phil S Baran
Journal:  Nat Chem       Date:  2009-06       Impact factor: 24.427

7.  The catalytic enantioselective total synthesis of (+)-liphagal.

Authors:  Joshua J Day; Ryan M McFadden; Scott C Virgil; Helene Kolding; Jennifer L Alleva; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-10       Impact factor: 15.336

8.  Palladium-Catalyzed Asymmetric Alkylation in the Synthesis of Cyclopentanoid and Cycloheptanoid Core Structures Bearing All-Carbon Quaternary Stereocenters.

Authors:  Allen Y Hong; Nathan B Bennett; Michael R Krout; Thomas Jensen; Andrew M Harned; Brian M Stoltz
Journal:  Tetrahedron       Date:  2011-12-30       Impact factor: 2.457

9.  Fusarisetin A: Scalable Total Synthesis and Related Studies.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Michelle H Lacoske; Chao-I Hung; Colin Jamora; Emmanuel A Theodorakis
Journal:  Chem Sci       Date:  2012-08-23       Impact factor: 9.825

10.  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

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