Synthesis of the macrocyclic core of laulimalide.
[figure: see text] A stereoselective synthesis of 3, corresponding to the fully functionalized macrocyclic core of the novel microtubule-stabilizing agent, laulimalide, has been completed. Efficient macrolactonization was achieved by a Mitsunobu reaction, installing the sensitive (Z)-enoate, and macrocyclic stereocontrol was then exploited to introduce the methyl group and trans-epoxide.
Paterson
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I
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K. ip100@cus.cam.ac.uk
De Savi
C
C
Tudge
M
M
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D018942:Macrolides; D008958:Models, Molecular; D008968:Molecular Conformation; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D043823:Taxoids
D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D018942:Macrolides; D043823:Taxoids; C117305:laulimalide; D017239:Paclitaxel