Alkoxide-accelerated sigmatropic rearrangements. A novel entry to the bicyclo[5.3.1]undec-7-ene system of the taxane diterpenes
β Scribed by Martin, Stephen F.; White, James B.; Wagner, Rolf
- Book ID
- 120938670
- Publisher
- American Chemical Society
- Year
- 1982
- Tongue
- English
- Weight
- 407 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Bicyclo[5.3.l]undecenone 2 corresponding to A and B rings in taxane diterpenes was synthesized. The eight-membered ring was constructed by a baseinduced intramolecular cyclization of twelve-membered lactam sulfoxides 15. 204 lja,b ya,bl,b2 isomer NC-S J K \*H,6 5 4 9 07 / 11' 1 3 10 -. 2 0 H R NHMe
The Cyclopropylalkylidenecyclopropane Thermal Double Ring Expansion. A Novel Route to the Bicyclo[5.3.1]undecane Skeleton of the AB Ring System of Taxanes. -The mechanism of the reaction is explained by the initial formation of a diradical followed by opening to a homoallylic biradical which closes