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Dearomatizing Cyclization of Arylsulfonylalkoxymethyl Lithiums: A Route to the Podophyllotoxin Skeleton

✍ Scribed by Clayden, Jonathan; Kenworthy, Martin N.; Helliwell, Madeleine

Book ID
121722674
Publisher
American Chemical Society
Year
2003
Tongue
English
Weight
176 KB
Volume
5
Category
Article
ISSN
1523-7060

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Pd-catalyzed route to (Β±)-podophyllotoxi
Pd-catalyzed route to (Β±)-podophyllotoxin skeleton. Synthesis of the aryltetralin derivative
✍ Lise Charruault; VΓ©ronique Michelet; Jean-Pierre GenΓͺt πŸ“‚ Article πŸ“… 2002 πŸ› Elsevier Science 🌐 French βš– 96 KB

A new Pd-catalyzed route to (Β±)-podophyllotoxin is disclosed. The strategy is based on an efficient organoaqueous reaction that diastereoselectively introduces the C-4 hydroxyl group and the furan ring. Further functionalization led to an iododerivative, which was cyclized under optimized conditions