Total synthesis and biological evaluation of 11-desmethyllaulimalide, a highly potent simplified laulimalide analogue.
[reaction: see text] A step-economical synthesis of 11-desmethyllaulimalide (2) is reported. This simplified analogue is available through an improved second-generation synthetic approach to the laulimalides, in a shorter step count and from much less expensive starting material than the parent compound. This new lead retains the anticancer function of laulimalide.
Departments of Chemistry and Molecular Pharmacology, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu
Paul A
PA
Wender
Michael K
MK
Hilinski
Nicolas
N
Soldermann
Susan L
SL
Mooberry
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000191:economics / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D018942:Macrolides; D015394:Molecular Structure; D017239:Paclitaxel / Q000494:pharmacology; D013329:Structure-Activity Relationship; D043823:Taxoids / Q000138:chemical synthesis / Q000737:chemistry / Q000191:economics / Q000494:pharmacology
C515623:11-desmethyllaulimalide; D000970:Antineoplastic Agents; D018942:Macrolides; D043823:Taxoids; C117305:laulimalide; D017239:Paclitaxel