Can someone explain this metabolization?

[Synaps3]

Can someone explain why there are two expoxides forming in this metabolization?
I am a noob and number VI doesn't make sense.

Does this mean any tertiary alcohol (such as 2m2b) would first be converted to an epoxide and then to a diol or are both of these epoxides the result of the chloro-vinyl?

BTW I know this is a very nasty drug, but I'm trying to figure out if any tertiary alcohol would form an epoxide at some stage.

http://oi66.tinypic.com/mkg9lf.jpg

 

[farmacista]

the conversion of the tertiary alcohol X to VI is synthetic (NaOH in THF) while olefin III in vivo could be converted to epoxide V or VI depending on which of the double bound reacts. The metabolic formation of an epoxide from a double bound it's not uncommon, but this doesn't happens with any tertiary alcohol.

 

[Synaps3]

Thanks for the info!

but this doesn't happens with any tertiary alcohol.

Good, so both those epoxides they show were because of the double bond.