Boron trifluoride-catalyzed reaction of 13-4(20)-epoxy-5-O-triethylsilyltaxinine A (1) gave the 3,5-diene (3) and the 3,8-cyclopropane (4) derivatives, while the similar reaction of the corresponding {x-4(20)-epoxide (2) afforded the ring contracted derivative (5) and its hemiacetal dimer (6). Plaus
Steroids part V reaction of cholesterol α-epoxide with boron trifluoride
✍ Scribed by I.G. Guest; B.A. Marples
- Publisher
- Elsevier Science
- Year
- 1969
- Tongue
- French
- Weight
- 210 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
The greater yield (61%) of the 6-ketone (2a) from 3a-acetoxy-5,6a-epoxy-5a-cholestane (la) compared with the yield (34%) of B-ketone (2b) from the corresponding 3-deoxy compound has been ascribed' to the energetically favourable conformational change, involving the 3-acetoxy group, in the formation
Reaction of the tricyclic epoxides (la) and (lb) with boron trifluoride etherate leads to fluorohydrins (2a) and (2v derived in the novel fluoride transfer, whereas (lc) undergoes isomerizationto Spiro ketone (3).
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