K. A. Jørgensen et al.
3.3, 4.0, 11.6 Hz, 1H), 3.07 (dd, J=11.6, 15.4 Hz, 1H), 2.75 ppm (dd, J=
4.0, 15.4 Hz, 1H); 13C NMR ([D4]MeOH): d=175.3, 135.5, 132.1, 130.1,
128.1, 127.8, 127.8, 73.5, 70.5, 57.0, 43.6, 29.9 ppm; HRMS (TOF ES+):
[5] a) Z.-X. Feng, W.-S. Zhou, Tetrahedron Lett. 2003, 44, 497; b) G.
Heimgärtener, D. Raatz, O. Reiser, Tetrahedron 2005, 61, 643.
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Angew. Chem. 1990, 102, 206; Angew. Chem. Int. Ed. Engl. 1990, 29,
205.
m/z calcd for C12H13NO3Na: 242.0788 [M+Na]+; found: 242.0786; [a]2D5
À86.2 (c=0.38 in MeOH).
=
(1R,2S,10aS)-1,2-Dihydroxy-1,2,3,5,10,10a-hexahydrobenzo[f]indolizine
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(13): BH3·Me2S (0.08 mL, 0.8 mmol) was added to a solution of 12
(13 mg, 0.059 mmol) in THF (2 mL) at 08C. The mixture was stirred
overnight, then EtOH (5 mL) was added slowly and the solution was re-
fluxed for 5 h. After removal of the solvents, the crude mixture was treat-
ed with EtOH (35 mL). After evaporation of solvent under reduced
pressure, the mixture was purified by column chromatography (eluent
1
EtOH/EtOAc 1:9) to give the product (9.2 mg, 71% yield). H NMR: d=
7.25–7.13 (m, 3H), 7.04 (d, J=6.8 Hz), 4.34 (unresolved dd, 1H), 4.20
(unresolved dd, 1H), 4.08 (d, J=14.4 Hz, 1H), 3.39 (d, J=14.4 Hz, 1H),
3.18 (t, J=10.4 Hz, 1H), 3.13 (d, J=16.4 Hz, 1H), 2.80 (d, J=16.4 Hz,
1H), 2.50 (m, 1H), 2.43 ppm (m, 1H); 1H NMR ([D6]DMSO): d=7.20–
7.06 (m, 4H), 4.81 (brd, J=4.8 Hz, 1H), 4.50 (brs, 1H), 4.19 (unresolved
q, 1H), 3.99 (t, J=5.2 Hz, 1H), 3.94 (d, J=14.6 Hz), 3.35 (brs, 1H), 3.27
(d, J=14.6 Hz, 1H), 3.04 (dd, J=11.6, 16.0 Hz, 1H), 2.97 (dd, J=0.8,
9.6 Hz, 1H), 2.63 (dd, J=3.6, 16.0 Hz, 1H), 2.40 (t, J=8.4 Hz, 1H),
2.33 ppm (brs, 1H); 13C NMR ([D6]DMSO): d=134.8, 134.4, 128.9, 126.2,
126.0, 125.3, 70.6, 68.8, 63.4, 61.2, 55.0, 28.3 ppm; HRMS (TOF ES+):
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m/z calcd for C12H15NO2Na: 228.0995 [M+Na]+; found: 228.0993; [a]2D5
À27.1 (c=0.25 in acetone).
=
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Acknowledgements
This work was made possible by a grant from The Danish National Re-
search Foundation. A.L. thanks Eusko Jaurlaritza/Gobierno Vasco for fi-
nancial support (postdoctoral fellowship), A.M. thanks NordForsk for fi-
nancial support, and G.B. thanks UV and MEC (Spanish Government).
Thanks are expressed to Dr. Jacob Overgaard for performing the X-ray
analysis.
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