Protecting a Double-Bond

[Tricosane]

I've been trying to figure out a way to theoretically synthesize Testosterone (or if that fails, Androstenedione) from Progesterone. I've run into a bit of a snag, though. I intend to turn a C-C single bond into a C=C bond, then break it via ozonolysis. However, the molecule has a pre-existing C=C double bond elsewhere that would also be broken. Do you know of any way to protect that double bond? Any sort of protecting groups out there?

[Tricosane]

I've been trying to figure out a way to theoretically synthesize Testosterone (or if that fails, Androstenedione) from Progesterone. I've run into a bit of a snag, though. I intend to turn a C-C single bond into a C=C bond, then break it via ozonolysis. However, the molecule has a pre-existing C=C double bond elsewhere that would also be broken. Do you know of any way to protect that double bond? Any sort of protecting groups out there?

[Tricosane]

I've been trying to figure out a way to theoretically synthesize Testosterone (or if that fails, Androstenedione) from Progesterone. I've run into a bit of a snag, though. I intend to turn a C-C single bond into a C=C bond, then break it via ozonolysis. However, the molecule has a pre-existing C=C double bond elsewhere that would also be broken. Do you know of any way to protect that double bond? Any sort of protecting groups out there?

[FUTI]

Try addition of bromine over double bond, then ozonolysis, and after that remove the bromine with zinc forming the double bond again.

[FUTI]

Try addition of bromine over double bond, then ozonolysis, and after that remove the bromine with zinc forming the double bond again.