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. 2014 Jul 8;136(30):10814–10820. doi: 10.1021/ja505639u

Scheme 4. Synthesis of cis-Epoxyhomoallylic Alcohol 19.

Scheme 4

Reagents and conditions: (a) (S,S)-Noyori (5 mol %), Et3N, HCO2H, rt, 83%, >95% ee; (b) H2N(CH2)3NH2, KH, 15 °C to rt, 80%; (c) TBSCl, imidazole, DMF, rt, 97%; (d) n-BuLi, HPMA, THF, −20 °C; C6H13I, −20 °C to rt, 88%; (e) TBAF, THF, rt, 96%; (f) Pd/CaCO3, quinoline, H2 (1 atm), MeOH, rt, 96%; (g) t-BuOOH, VO(acac)2 (2 mol %), CH2Cl2, 0 °C, 94%, 92% dr. KAPA = potassium 3-aminopropylamide, TBSCl = tert-butyldimethylsilyl chloride, HMPA = hexamethyl phosphoramide, TBAF = tetra-n-butylammonium fluoride.