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

Scheme 8. Synthesis of Stereoisomeric Epoxides from 19.

Scheme 8

Reagents and conditions: (a) N-Cbz-d-leucine, DCC, DMAP, CH2Cl2, rt, 96%; (b) Pd/C (10% wt/wt), H2 (1 atm), THF, rt; DCC, formic acid, CH2Cl2, rt, 82%; (c) N-formyl-l-leucine, DIAD, PPh3, THF, 0 °C to rt, 82%; (d) N-Cbz-d-leucine, DIAD, PPh3, THF, 0 °C, 93%; (e) Pd/C (10% wt/wt), H2 (1 atm), THF, rt; DCC, formic acid, CH2Cl2, rt, 67%.