Total synthesis of luminacin D.
[reaction: see text] A highly convergent synthesis of the angiogenesis inhibitor luminacin D has been achieved in 13 linear steps (19 steps total, 5.3% overall yield) utilizing a samarium(II) iodide-mediated mixed tandem aldol/Evans-Tishchenko reaction to construct the carbohydrate precursor. The modular synthetic design will allow derivatization at key positions necessary for biochemical mode of action studies.
Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
J Brad
JB
Shotwell
Evan S
ES
Krygowski
John
J
Hines
Brian
B
Koh
Elliott W D
EW
Huntsman
Hui Won
HW
Choi
John S
JS
Schneekloth
John L
JL
Wood
Craig M
CM
Crews
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000494:pharmacology; D002417:Cattle; D002455:Cell Division / Q000187:drug effects; D004730:Endothelium, Vascular / Q000166:cytology; D020128:Inhibitory Concentration 50; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D020533:Angiogenesis Inhibitors; D001547:Benzaldehydes; D013141:Spiro Compounds; C413565:luminacin D