Stereoselective Synthesis of the C1−C13 Fragment of (+)-Discodermolide Using Asymmetric Allyltitanations
✍ Scribed by BouzBouz, Samir; Cossy, Janine
- Book ID
- 120320463
- Publisher
- American Chemical Society
- Year
- 2003
- Tongue
- English
- Weight
- 80 KB
- Volume
- 5
- Category
- Article
- ISSN
- 1523-7060
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The C1-C13 fragment of bistramide A was prepared from 5-hexenoic acid in 15 linear steps and in 16% overall yield. The core 2,6-trans-tetrahydropyran ring was obtained via a kinetically controlled oxa-Michael cyclization from the corresponding chiral a,b-unsaturated hydroxyester. This precursor was
The C1-C8 and C9--C24 fragments of (-)-discodermolide, the antipode of the marine natural product (+)discodermolide, have been synthesized with excellent stereoselectivities. These syntheses feature the utilization of the isoxazolidine-mediated asymmetric alkylation methodology and fragment-fragment