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. 2015 Sep 1;54(43):12618–12621. doi: 10.1002/anie.201506366

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© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Scheme 5 — Reagents and conditions: a) OsO₄ (2 mol %), NMO, acetone/H₂O (3:1), RT, 3 h; b) NaIO₄/SiO₂, CH₂Cl₂, RT, 15 min, 85 % (2 steps); c) ZnCl₂, SOCl₂, CDCl₃, RT, 3 h; d) 29, ZnCl₂, CH₂Cl₂, −30 °C→RT, 12 h, 38 % of 1 and 33 % of 30 (2 steps). NMO=N-methylmorpholine-N-oxide, TIPS=triisopropylsilyl.