- Reaction of 6e and 6f with PhSeH and Pyridine. Selenoxide 6e (9.53 mg) in CH2C12 (1 ml) was reacted with PhSeH (100 mg, 0.6 mmol) and pyridine (10 pl, ca. 0.1 mmol) for 70 h at r.t. The soln. was evaporated and the residue purified by column chromatography (silica gel, CHCI,) to yield 6.6 mg of6b.
The same procedure with selenone 6e (6.3 mg) afforded 2.4 mg of 6b.
- Reduction of 3b. To lithium naphthalenide prepared from naphthalene (0.46 g, 3.6 mmol) and Li (0.02 g, 3.6 mmol) in HMPA (5.0 ml) [23], a soh. of 3b (0.6 mmol) in furan (80 ml) was added at -70". The soh. was stirred 3 hat -70", then 5 hat -50" and 10 h a t r.t. After decomposition with EtOH (2.0 ml) at o", the mixture was worked up as usual. Two successive purifications by flash chromatography (silica gel, AcOEt, then CHCl,/hexane 1 :lo) afforded 2d (26%) [7] and 15 (22%) [4], both identified by comparison of their 'H-NMR with those reported.