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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


Total synthesis of (±) podophyllotoxin
✍ T Kaneko; H Wong 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 166 KB

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