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. Author manuscript; available in PMC: 2012 Jul 31.
Published in final edited form as: J Am Chem Soc. 2008 Dec 3;130(48):16295–16309. doi: 10.1021/ja804659n

Scheme 9.

Scheme 9

Synthesis of the tetrahydropyran 59. Reagents and conditions: a) KOt-Bu, DMSO, 70 °C, 70%; b) 2-propenylMgBr, THF/Et2O, −78 °C, 80%; c) 15 (2 mol%), 3Å MS, Et2O, −40 °C, dr 94:6, 97% ee, 84% 60; d) H2 (1 atm), Pd/C (5 mol%), EtOAc, dr 98:2, 95% 59. See ref31 for abbreviations.