[Humr]

Hello. I would like to ask if someone has idea what to use instead of tert-Butyl hydroperoxide in this reaction. I work with betuline and i cannot use peroxides because epoxide between C20 and C29 would form.

[rolnor]

What reaction do you want to do with betuline?

[Humr]

I want to have COOH on C30. I do this reaction only with SeO2 in glym. It does alhehyde on C30. I would be glad if i could skip second oxidation.

[rolnor]

Have checked Scifinder or Reaxys? It seems this should be possible to solve.
Here is a link, they use t-BuOOH but dont get epoxidation?
One more thing; If you do get epoxide you can convert it back to alkene with PPh3.

[Humr]

Betuline is what i want to use. Reaction below is what i found in some literature. That is interesting idea.  So are you suggesting to use SeO2, T-BuOOH and PPh3 at once?

I have some idea too. How i normally do this reaction is: Disolve betuline in 2-metoxyethanol, add 2 eq. SeO2 and reflux for 4h.

What if i add Fehling's solution to this reaction?

[rolnor]

No, if you get epoxide you isolate this and treat with PPh3.
I think its better to include oxidation of the aldehyde as avseparate step, there are manyways to do this and yields should be high.