I need to cleave an alkene on a complex molecule. The reagent should be less toxic than OsO4.
Only a catalytic amount of OsO4 is needed, you can use NMO (stoichiometric amount) to reoxidize it.
Ozonolysis under Zn/H+ you have to find out the condition follow article relate to ozonolysis with Zn.
There are a couple of ppaers dealing with the use of RuCl3 and CeCl3 and K/NaIO4 as oxidant. This should give you a diol, which can be further cleaved and oxidized to the aldehyde with KIO4.
Once I used a stochiometric amount KMnO4 to convert an alkene to a diol in MeOH/water mixture at low temperature (ice bath). Then you can cleave the diol with NaIO4.
sodium periodate on wet silica gel is very easy, simply filter off your aldehyde in DCM, works a treat. high yielding
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