Synthesis of the C15–C27 fragment of the antitumor agent laulimalide
✍ Scribed by E.Kate Dorling; Elisabeth Öhler; Johann Mulzer
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 129 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A stereocontrolled synthesis of the C15±C27 fragment of laulimalide is described. Key features are a divergent±convergent synthesis from (R)-glycidol, an interesting formation of a trisubstituted double bond via ring closing metathesis with Grubbs' ruthenium catalyst and a site selective protection of a syn-1,2-diol.
📜 SIMILAR VOLUMES
The C 15 -C 28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps from known epoxide 5, with an overall yield of 16%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry. The 19,2
A stereocontrolled synthesis of the title compound is described. Key steps are an allylsilane addition to a chiral acetal as the major coupling step and a Yamaguchi macrolactonization for ring closure.