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.
Wender
Paul A
PA
Departments of Chemistry and Molecular Pharmacology, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu
Hilinski
Michael K
MK
Soldermann
Nicolas
N
Mooberry
Susan L
SL
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