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(
S
)-1,3-Dihydroxy-8-methyl-8,9-dihydro-5
H
-7-oxa-benzocyclodecene-6,12-dione
(Sporostatin, 1)
Iodine (0.52 g, 2.06 mmol) was added
to a mixture of aluminum (0.074 g, 2.76 mmol) in dry benzene. The
mixture was refluxed for 1 h, cooled to r.t., and then n-Bu4N+I- (0.0032
g, 0.0089 mmol) and compound 10 (0.020
g, 0.688 mmol) in dry benzene (8 mL) were added. The mixture was stirred
for 45 min at 10 ˚C and quenched with H2O.
After acidification with 2 M HCl, the mixture was extracted with EtOAc
(3 × 10 mL). The organic phase was washed
with brine, dried over Na2SO4, filtered, and
concentrated in vacuo. The residue was purified by flash chromatography
on SiO2 (hexanes-EtOAc, 1:1) to afford the sporostatin
(1, 0.017 mg, 95%) as white solid,
mp 198-200 ˚C; [α]D
²5 -18.8 (c 0.5, MeOH). ¹H
NMR (300 MHz, DMSO): δ = 13.59 (s, 1 H), 10.75
(s, 1 H), 6.80 (d, 1 H, J = 15.8
Hz), 6.32 (s, 1 H), 6.22 (s, 1 H), 5.92-5.98 (m, 1 H),
5.01-5.11 (m, 1 H), 4.07 (d, 1 H, J = 16.8
Hz), 3.82-3.90 (m, 1 H), 2.54-2.58 (m, 1 H), 1.36
(d, 3 H, J = 6.5
Hz). ¹³C NMR (75 MHz, DMSO):
δ = 198,
173.1, 167.4, 163.7, 140.0, 138.2, 136.3, 114.5, 111.7, 102.1, 74.9,
43.9, 41.6, 19.6. IR (neat): ν = 3424, 2255, 2128,
1739, 1650, 1376 cm-¹. MS (LC-MS): m/z = 263 [M + 1]+.
HRMS: m/z calcd for C14H15O4:
263.0919; found: 263.0916.
