Total Synthesis of the Microtubule-Stabilizing Agent (−)-Laulimalide
- 6 September 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (20) , 3149-3152
- https://doi.org/10.1021/ol010150u
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.Keywords
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