Enantioselective total synthesis of (−)-epipodophyllotoxin and (−)-podophyllotoxin
✍ Scribed by R. Van Speybroeck; H. Guo; J. Van der Eycken; M. Vandewalle
- Book ID
- 104204011
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 638 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
An enantioselective total synthesis of (-)-epipodophyllotoxin (2) and hence of (-)-podophyllotoxin (I) is described, involving as key steps a conjugate addition on butenolide 13 as the chiral template, a stereoselective aldol condensation on lla and a stereoselective ring closure of 8.
📜 SIMILAR VOLUMES
A straightforward approach to podophyllotoxin was developed using silyl enol ether 5. Podophyllotoxin (1) is a lignan isolated from Podophyllum peltatum and p. ml. It is a potent inhibitor of microtubule assembly and a key intermediate of an antitumor agent, etoposide (2)'. Although there have bee