title: Total synthesis of (-)-dihydroprotolichesterenic acid via diastereoselective conjugate addition to chiral fumarates.
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.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712.
authors.forename: J Caleb
authors.initials: JC
authors.lastname: Hethcox
authors.forename: Charles S
authors.initials: CS
authors.lastname: Shanahan
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin
keywords: Butyrolactone; Chiral Auxiliary; Conjugate addition; Succinate; Total Synthesis
references.citation: Angew Chem Int Ed Engl. 2006 Oct 27;45(42):7083-6
references.pmid: 17009377
references.citation: J Org Chem. 1996 Sep 6;61(18):6450-6453
references.pmid: 11667493
references.citation: J Nat Prod. 2004 Jan;67(1):46-8
references.pmid: 14738384
references.citation: Tetrahedron Lett. 2011 Aug 10;52(32):4076-4079
references.pmid: 21857754
references.citation: Invest Ophthalmol. 1974 Apr;13(4):296-9
references.pmid: 4818814
references.citation: J Org Chem. 2002 Mar 22;67(6):1738-45
references.pmid: 11895386
references.citation: J Am Chem Soc. 1948 Nov;70(11):3724-6
references.pmid: 18102930
references.citation: J Am Chem Soc. 2001 May 16;123(19):4480-91
references.pmid: 11457234
references.citation: J Am Chem Soc. 2008 Aug 27;130(34):11546-60
references.pmid: 18680297
references.citation: Org Lett. 1999 Sep 23;1(6):865-8
references.pmid: 10823215