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6 To a well-stirred solution of TBS-dithiane 3 (120 mg, 0.51 mmol) in Et2O
(2 mL), t-BuLi was added (1.7 M in hexane, 0.43
mL) via syringe at -78 ˚C. The reaction mixture
was stirred for 1 h at -40 ˚C. Then, a solution
of epoxide 5
(1 mmol) in Et2O
(1 mL) was added to the reaction mixture at -78 ˚C.
The mixture was allowed to warm to 0 ˚C over
1
h and then recooled to -78 ˚C. A solution of epoxide 4 (1.1 mmol) in Et2O-HMPA
(90 mg HMPA in 1 mL of Et2O) was added. The reaction
mixture was stirred from -78 to 0 ˚C overnight,
then quenched with sat. aq NH4Cl (1 mL). After dilution
of the mixture with Et2O, the organic layer was separated.
The aqueous phase was extracted three times with Et2O,
and the combined organic layers were dried over MgSO4,
filtered, and concentrated under reduced pressure. Flash chromatography
(hexanes-EtOAc, 30:1) provided
(-)-8 in 74% yield. IR: 3424, 2952,
1255, 1099 cm-¹. ¹H NMR
(300 MHz, CDCl3): δ = 7.38-7.26
(m, 10 H), 5.12
(d, J = 7.2
Hz, 1 H), 4.53 (d, J = 2.7
Hz, 1 H), 4.52 (s, 2 H), 4.43-4.40 (m, 1 H), 3.63 (t, J = 6.3 Hz,
2 H), 2.79-2.72
(m, 4 H), 2.47-2.36
(m, 4 H), 1.97-1.90 (m, 4 H), 0.92 (s,
9 H),
0.18 (s, 3 H), 0.16 (s, 3 H). ¹³C NMR
(75 MHz, CDCl3): δ = 145.6, 138.2,
128.3, 128.2, 127.7, 127.5, 126.8, 125.5, 73.2, 70.1, 69.2, 66.8,
51.6, 49.2, 43.6, 38.7, 26.3, 26.1, 25.9, 25.0, 18.1, -3.1, -4.5; [α]²5
D -41.5
(c 0.6, CHCl3). ESI-MS: m/z = 555.9 [M + Na]+.
HRMS: m/z calcd for calcd for
C29H45O3S2Si: 533.2579;
found: 533.2587 [M + H]+.
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