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Total synthesis of the microtubule-stabilizing agent (-)-laulimalide
I Paterson1, C De Savi, M Tudge
1University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cus.cam.ac.uk
Organic Letters
|September 28, 2001
Abstract:
[structure: see text] The total synthesis of the potent microtubule-stabilizing anticancer agent (-)-laulimalide has been achieved in 27 steps and 2.9% overall yield. Notable features are the use of Jacobsen HDA chemistry for the enantioselective construction of the side chain dihydropyran, a diastereoselective aldol coupling using chiral boron enolate methodology, a Mitsunobu macrolactonization, and a Sharpless AE to introduce the epoxide onto des-epoxy-laulimalide.