Synthesis of the taxane ring system
β Scribed by Holton, Robert A.
- Book ID
- 127150168
- Publisher
- American Chemical Society
- Year
- 1984
- Tongue
- English
- Weight
- 293 KB
- Volume
- 106
- Category
- Article
- ISSN
- 0002-7863
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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 stereoselective one-pot three-component coupling reaction was accomplished by 1,4-addition of the protected cyanohydrin ether 9f to cyclohexenone 10g and subsequent addition of the resulting enolate to formaldehyde in high yield for the formation of the AC ring system of taxanes. We found that t