Table 1. Screening of Conditions for Diepoxide Fragmentation.

entry	reagent	solvent	product(s)
1	PhSeNa		52 + 53
2	NaTeH		52 + 53
3	NaI/NaOAc/HOAc		no reaction
4	Zn/MeOH		52 + 53
5	SmI2		52 + 53
6	Li/naphthalene		52 + 53
7	Mg/MeOH		no reaction
8	N2H4		no reaction
9	Cr(OAc)2		decomposition
10	Pt/C, H2	ethyl acetate	55 + 56
11	Al–Hg	THF:EtOH:sat. NaHCO3 (2:1:0.15)	54 (15%) + 57
12	Al–Hg	THF:EtOH (2:1)	no reaction
13	Al–Hg	EtOH:sat. NaHCO3 (1:0.15)	54 (<5%) + 57
14	Al–Hg	sat. NaHCO3	54 (51%) + 57
15	Al–Hg (portion-wise addition)	sat. NaHCO3	54 (64%; 56%a)
16	Al–Hg	sat. K2CO3	no reaction
17	Al–Hg	sat. LiCl	no reaction
18	Al–Hg	sat. NaCl	54 (<10%) + 57
19	Al–Hg	sat. NH4Cl	54 (19%) + 57
20	Al–Hg	pH 7.4 buffer	54 (41%) + 57

^aGram-scale reaction.