title: Enantioselective total synthesis of all of the known chiral cleroindicins (C-F): clarification among optical rotations and assignments.
abstract: Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.
authors.affiliation: Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106, USA.
authors.forename: Todd A
authors.initials: TA
authors.lastname: Wenderski
authors.forename: Shenlin
authors.initials: S
authors.lastname: Huang
authors.forename: Thomas R R
authors.initials: TR
authors.lastname: Pettus
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis*; D009904:Optical Rotation; D013237:Stereoisomerism
chemical_list: D001547:Benzaldehydes; D001572:Benzofurans; C534626:cleroindicin C; C525723:cleroindicin D; C542746:cleroindicin E; C534625:cleroindicin F