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.
Shotwell
J Brad
JB
Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
Krygowski
Evan S
ES
Hines
John
J
Koh
Brian
B
Huntsman
Elliott W D
EW
Choi
Hui Won
HW
Schneekloth
John S
JS
Wood
John L
JL
Crews
Craig M
CM
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