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Studies directed towards the synthesis of taxane diterpenes: A remarkable rearrangement

✍ Scribed by Jeffrey D. Winkler; John P. Hey; Stephen D. Darling

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
232 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Acid-catalyzed fragmentation of the intramolecular dioxolenone photocycloaddition product 9 leads not to 10, the desired taxane skeleton, but instead to the remarkable rearrangement product 11.

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Synthesis of bridged nine-membered ring
Synthesis of bridged nine-membered ring ethers: Studies directed towards the synthesis of eunicellin-based marine diterpenes
✍ M. Nowakowski; H.M.R. Hoffmann πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 410 KB

A concise annulation-fragmentation strategy has been elaborated for the construction of the bridged nine-membered ring ether moiety of the eunicelline diterpenes. Key steps are a SmI:-induced Barbier cyclization and an oxidative ring fission using cerium(IV) ammonium nitrate (CAN)