title: Enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a diastereoselective aldol/beta-elimination sequence: application to the C(15)-C(21) fragment of tedanolide C.
abstract: An enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a highly diastereoselective, one-pot syn-aldol and beta-elimination sequence utilizing the chiral beta-(phenylselenyl)propionyl imide 15 is described. This new method, which constitutes an alternative to the Baylis-Hillman reaction, has been applied to the synthesis of the C(15)-C(21) fragment of tedanolide C.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Scripps Florida, 130 Scripps Way, Jupiter, Florida 33458, USA.
authors.forename: Roland
authors.initials: R
authors.lastname: Barth
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D007094:Imides; D007659:Ketones; D018942:Macrolides; C516408:tedanolide C
references.citation: Bioorg Med Chem. 2005 Jan 17;13(2):455-62
references.pmid: 15598567
references.citation: J Nat Prod. 2007 Jul;70(7):1133-8
references.pmid: 17564468
references.citation: Nat Protoc. 2007;2(10):2451-8
references.pmid: 17947986
references.citation: Chem Rev. 2003 Mar;103(3):811-92
references.pmid: 12630854
references.citation: Chem Commun (Camb). 2009 Oct 7;(37):5496-514
references.pmid: 19753340
references.citation: J Org Chem. 2006 Mar 17;71(6):2510-3
references.pmid: 16526806
references.citation: J Org Chem. 2005 Mar 18;70(6):2329-31
references.pmid: 15760223