title: Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions.
abstract: An efficient and asymmetric synthetic approach towards one of the biologically interesting 4(S)-11-diHDHA derivatives was developed. This process mainly relied on two reactions, one is the copper-catalyzed mild cross-coupling that allows for the efficient construction of a chiral α-alkynyl α-hydroxy motif and another is the synthesis of chiral α-hydroxy α-stannanes that has previously been developed by our group featuring the asymmetric stannylation using the well-established tributyltin hydride/diethyl zinc system from an aldehyde.
authors.affiliation: Division of Chemistry, Department of Biochemistry University of Texas Southwestern Medical Center 5323 Harry Hines Blvd., Dallas, Texas 75390-9038, USA. shairwang@gmail.com.
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
authors.forename: Anyu
authors.initials: A
authors.lastname: He
authors.forename: Errabelli
authors.initials: E
authors.lastname: Ramu
authors.forename: John R
authors.initials: JR
authors.lastname: Falck
mesh_terms: D004281:Docosahexaenoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017971:Tin Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C000601332:4(S)-11-dihydroxydocosahexaenoic acid; D017971:Tin Compounds; C031525:stannane; D004281:Docosahexaenoic Acids