Literature DB >> 26273115

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

J Caleb Hethcox1, Charles S Shanahan1, Stephen F Martin1.   

Abstract

Recent studies of diastereoselective conjugate additions of monoorganocuprates, Li[RCuI], to chiral γ-alkoxycrotonates and fumarates are disclosed. This methodology was applied to the shortest total synthesis of (-)-dihydroprotolichesterinic acid to date, but several attempts to prepare other succinate-derived natural products, such as pilocarpine and antrodin E, were unsuccessful.

Entities:  

Keywords:  Chiral Auxiliary; Conjugate Addition; Cuprate; Succinate; Total Synthesis

Year:  2015        PMID： 26273115      PMCID： PMC4528386          DOI： 10.1016/j.tet.2015.05.023

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  24 in total

1.  Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline.

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Authors:  Matthew P Glenn; Sung-Youn Chang; Oliver Hucke; Christophe L M J Verlinde; Kasey Rivas; Carrie Hornéy; Kohei Yokoyama; Frederick S Buckner; Prakash R Pendyala; Debopam Chakrabarti; Michael Gelb; Wesley C Van Voorhis; Saïd M Sebti; Andrew D Hamilton
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3.  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

4.  An evaluation of the pilocarpine Ocusert.

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

5.  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

6.  An entry to a chiral dihydropyrazole scaffold: enantioselective [3 + 2] cycloaddition of nitrile imines.

Authors:  Mukund P Sibi; Levi M Stanley; Craig P Jasperse
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

7.  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

8.  Ni(II) Tol-BINAP-catalyzed enantioselective Michael reactions of beta-ketoesters and unsaturated N-acylthiazolidinethiones.

Authors:  David A Evans; Regan J Thomson; Francisco Franco
Journal:  J Am Chem Soc       Date:  2005-08-10       Impact factor: 15.419

9.  Low-temperature Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds.

Authors:  Toshinobu Korenaga; Aram Ko; Kazuaki Shimada
Journal:  J Org Chem       Date:  2013-09-13       Impact factor: 4.354

10.  (-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase.

Authors:  E Eich; H Pertz; M Kaloga; J Schulz; M R Fesen; A Mazumder; Y Pommier
Journal:  J Med Chem       Date:  1996-01-05       Impact factor: 7.446
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