Enantioselective total synthesis of all of the known chiral cleroindicins (C-F): clarification among optical rotations and assignments.
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.
Wenderski
Todd A
TA
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106, USA.
Huang
Shenlin
S
Pettus
Thomas R R
TR
D001547:Benzaldehydes / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis*; D009904:Optical Rotation; D013237:Stereoisomerism
D001547:Benzaldehydes; D001572:Benzofurans; C534626:cleroindicin C; C525723:cleroindicin D; C542746:cleroindicin E; C534625:cleroindicin F