Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.
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.
Mente
Nolan R
NR
Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA.
Wiemer
Andrew J
AJ
Neighbors
Jeffrey D
JD
Beutler
John A
JA
Hohl
Raymond J
RJ
Wiemer
David F
DF
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
D000972:Antineoplastic Agents, Phytogenic; D004273:DNA, Neoplasm; D013267:Stilbenes; C518723:schweinfurthin F; D013936:Thymidine