Literature DB >> 23539490

Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates.

J Caleb Hethcox1, Charles S Shanahan, Stephen F Martin.   

Abstract

A diastereoselective conjugate addition of a variety of monoorganocuprates, Li[RCuI], to chiral fumarates to provide funtionalized succinates has been developed. The utility of this reaction is demonstrated in a concise total synthesis of (-)-dihydroprotolichesterenic acid that required only four steps and proceeded in an overall 31% yield.

Entities:  

Keywords:  Butyrolactone; Chiral Auxiliary; Conjugate addition; Succinate; Total Synthesis

Year:  2013        PMID： 23539490      PMCID： PMC3607549          DOI： 10.1016/j.tetlet.2013.02.014

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

1.  Efficient Stereoselective Synthesis of the Enantiomers of Highly Substituted Paraconic Acids.

Authors:  Tomás Martín; Carmen M. Rodríguez; Victor S. Martín
Journal:  J Org Chem       Date:  1996-09-06       Impact factor: 4.354

2.  Five new maleic and succinic acid derivatives from the mycelium of Antrodia camphorata and their cytotoxic effects on LLC tumor cell line.

Authors:  Norio Nakamura; Akiko Hirakawa; Jiang-Jing Gao; Hiroko Kakuda; Motoo Shiro; Yasuhiro Komatsu; Chia-chin Sheu; Masao Hattori
Journal:  J Nat Prod       Date:  2004-01       Impact factor: 4.050

3.  Intermolecular oxidative enolate heterocoupling.

Authors:  Phil S Baran; Michael P DeMartino
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-27       Impact factor: 15.336

4.  Lactone aliphatic acids as antibacterial agents.

Authors:  C J CAVALLITO; D M FRUEHAUF; J H BAILEY
Journal:  J Am Chem Soc       Date:  1948-11       Impact factor: 15.419

5.  Catalytic enantioselective Michael additions to unsaturated ester derivatives using chiral copper(II) Lewis acid complexes.

Authors:  D A Evans; M C Willis; J N Johnston
Journal:  Org Lett       Date:  1999-09-23       Impact factor: 6.005

6.  An evaluation of the pilocarpine Ocusert.

Authors:  D M Worthen; T J Zimmerman; C A Wind
Journal:  Invest Ophthalmol       Date:  1974-04

7.  Toward a total synthesis of the stemofoline alkaloids: Advancement of a 1,3-dipolar cycloaddition strategy.

Authors:  Charles S Shanahan; Nathan O Fuller; Bjoern Ludolph; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-08-10       Impact factor: 2.415

8.  Enantioselective and diastereoselective Mukaiyama-Michael reactions catalyzed by bis(oxazoline) copper(II) complexes.

Authors:  D A Evans; K A Scheidt; J N Johnston; M C Willis
Journal:  J Am Chem Soc       Date:  2001-05-16       Impact factor: 15.419

9.  Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid.

Authors:  Mukund P Sibi; Pingrong Liu; Jianguo Ji; Saumen Hajra; Jian-xie Chen
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

10.  Intermolecular enolate heterocoupling: scope, mechanism, and application.

Authors:  Michael P DeMartino; Ke Chen; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-08-05       Impact factor: 15.419
  10 in total
  2 in total

1.  Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy.

Authors:  Cassandra L Schrank; Michael W Danneman; Emily A Prebihalo; Robert E Anderson; Tyler J Gibson; William M Wuest; Richard J Mullins
Journal:  Tetrahedron Lett       Date:  2020-04-18       Impact factor: 2.415

2.  Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid.

Authors:  J Caleb Hethcox; Charles S Shanahan; Stephen F Martin
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457
  2 in total

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