Identify the reagents , and used for the following conversion:
The starting material is a cyclohexane ring carrying a group at C-, a group at the adjacent C-, and an group at C- — that is, methyl -[-hydroxy--(-oxoethyl)cyclohexyl]acetate. It is taken through three steps:
- : the same ring, now carrying at both C- and C-, with the C- untouched.
- : a bicyclic hydrindane — the two side chains have joined to close a five-membered ring fused to the cyclohexane — in which the new five-membered ring carries a bearing a group; the ring is still present.
- : the same bicyclic skeleton, with that group replaced by .
- A
, , , ethylene glycol
- B
, ,
- C
, , , ethylene glycol
- D
, ,
