Enantioselective synthesis of the C1C9 segment of bryostatin by kinetic resolution of racemic β-keto esters
✍ Scribed by Markus Kalesse; Marcus Eh
- Book ID
- 103408904
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 172 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
A stereocontrolled synthesis of the C 1 C 9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral b-alkoxy ketones to elaborate the syn-1,3-diol functionality and a
The @,yepoxy esters (\*)-2 to (f)-6 were synthetisized. The E-values of the kinetic resolution of 2, 3,4, and 6 with PLE and the absolute configuration of the products of the hydrolysis were determined by the conversion to known compounds.
A stereo-and enantioselective approach towards the C 1 -C 16 fragment of bryostatins is reported using Jacobsen's catalyst for kinetic resolution of a terminal epoxide, a Horner-Wadsworth-Emmons coupling reaction and a 1,4-Michael type cyclization as key steps.