title: Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.
abstract: Total synthesis of the (R,R,R)- and (S,S,S)-enantiomers of the natural product schweinfurthin F has been completed. Comparisons of spectral data and optical rotations with those reported for the natural product, as well as a variety of bioassay data, allow assignment of the natural material as the (R,R,R)-isomer.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA.
authors.forename: Nolan R
authors.initials: NR
authors.lastname: Mente
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Wiemer
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Neighbors
authors.forename: John A
authors.initials: JA
authors.lastname: Beutler
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Hohl
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004273:DNA, Neoplasm / Q000096:biosynthesis; D019665:Euphorbiaceae / Q000737:chemistry; D006801:Humans; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013936:Thymidine / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004273:DNA, Neoplasm; D013267:Stilbenes; C518723:schweinfurthin F; D013936:Thymidine