Synthesis of the C1C9 segment of epothilons
✍ Scribed by Eckhard Claus; Axel Pahl; Peter G. Jones; Hartmut M. Meyer; Markus Kalesse
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 174 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The CI-C9 segment of epothilons was generated by an aldol reaction between chiral aldehyde 3 and ethyl ketone 4. Removal of the TBS protecting groups and debenzylation generated spiro ketal 13 which was analyzed by X-ray crystallography.
📜 SIMILAR VOLUMES
The C( 1)-C(9) segment 3 of the macrolides epothilon A and B 1, two new cytotoxic natural products, has been synthesized in a direct manner. Key steps in the synthesis are a stereoselective aldol reaction of 6 and 7 and a Brown allylation of 9.
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