Literature DB >> 21271716

A catalytic, asymmetric formal synthesis of (+)-hamigeran B.

Herschel Mukherjee1, Nolan T McDougal, Scott C Virgil, Brian M Stoltz.   

Abstract

A concise asymmetric, formal synthesis of (+)-hamigeran B is reported. A Pd-catalyzed, decarboxylative allylic alkylation, employing a trifluoromethylated derivative of t-BuPHOX, is utilized as the enantioselective step to form the critical quaternary carbon center in excellent yield and enantioselectivity. The product is converted in three steps to a late-stage intermediate previously used in the synthesis of hamigeran B.

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Year:  2011        PMID: 21271716      PMCID: PMC3045637          DOI: 10.1021/ol102669z

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


  21 in total

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Authors:  K. C. Nicolaou; David Gray; Jinsung Tae
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-01       Impact factor: 15.336

2.  Stereospecific total synthesis of the antiviral agent hamigeran B--use of large silyl groups to enforce facial selectivity and to suppress hydrogenolysis.

Authors:  Derrick L J Clive; Jian Wang
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-28       Impact factor: 15.336

3.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

4.  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

5.  A short and concise asymmetric synthesis of hamigeran B.

Authors:  Barry M Trost; Carole Pissot-Soldermann; Irwin Chen
Journal:  Chemistry       Date:  2005-01-21       Impact factor: 5.236

6.  Deantiaromatization as a driving force in an electrocyclic reaction.

Authors:  Michael Harmata; Pinguan Zheng; Peter R Schreiner; Armando Navarro-Vázquez
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-13       Impact factor: 15.336

7.  Tandem conjugate reduction-aldol cyclization using Stryker's reagent.

Authors:  P Chiu; C P Szeto; Z Geng; K F Cheng
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

8.  Intramolecular alkynylogous mukaiyama aldol reaction starting from bicyclic alkanones tethered to alkynyl esters: formal total synthesis of (+/-)-hamigeran B.

Authors:  Laurence Miesch; Tania Welsch; Vincent Rietsch; Michel Miesch
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

9.  A facile and modular synthesis of phosphinooxazoline ligands.

Authors:  Kousuke Tani; Douglas C Behenna; Ryan M McFadden; Brian M Stoltz
Journal:  Org Lett       Date:  2007-05-31       Impact factor: 6.005

10.  Synthesis of (-)-hamigeran B.

Authors:  Douglass F Taber; Weiwei Tian
Journal:  J Org Chem       Date:  2008-09-05       Impact factor: 4.354

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  12 in total

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Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

3.  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

4.  Synthetic Studies toward the Hamigerans with a 6-7-5 Tricyclic Core.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  Org Lett       Date:  2020-05-13       Impact factor: 6.005

5.  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

6.  11-Step and Scalable Total Synthesis of Hamigeran M Enabled by Five C-H Functionalizations.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 16.383

7.  The reaction mechanism of the enantioselective Tsuji allylation: inner-sphere and outer-sphere pathways, internal rearrangements, and asymmetric C-C bond formation.

Authors:  John A Keith; Douglas C Behenna; Nathaniel Sherden; Justin T Mohr; Sandy Ma; Smaranda C Marinescu; Robert J Nielsen; Jonas Oxgaard; Brian M Stoltz; William A Goddard
Journal:  J Am Chem Soc       Date:  2012-11-06       Impact factor: 15.419

8.  Development of asymmetric deacylative allylation.

Authors:  Alexander J Grenning; Christie K Van Allen; Tapan Maji; Simon B Lang; Jon A Tunge
Journal:  J Org Chem       Date:  2013-07-01       Impact factor: 4.354

9.  The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis.

Authors:  Allen Y Hong; Brian M Stoltz
Journal:  European J Org Chem       Date:  2013-05-01

10.  Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.

Authors:  Zackaria Nairoukh; Gunda G K S Narayana Kumar; Yury Minko; Ilan Marek
Journal:  Chem Sci       Date:  2016-09-15       Impact factor: 9.825

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