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. Author manuscript; available in PMC: 2018 Nov 15.
Published in final edited form as: Synthesis (Stuttg). 2002;2002(3):371–374. doi: 10.1055/s-2002-20037

Scheme.

Scheme

(a) H2, Pd(OH)2, EtOAc, 91%; (b) PhCH(OMe)2, p-TsOH, CH2Cl2, 91%; (c) (COCl)2, DMSO, Et3N, CH2Cl2, −78 °C; (d) Ph3P=CHCHO, benzene, reflux, 70% for 2 steps; (e) CH2=CHMgBr, Et2O, 0 °C; (f) Ac2O, Et3N, DMAP, CH2Cl2, 74% for 2 steps; (g) Pd(PPh)4, NaN3, THF–H2O, 65 °C, 81%; (h) NaOH, MeOH–H2O; (i) N-methylmorpholine, isobutyl chloroformate, serine methyl ester · HCl, THF, −30 to +23 °C, 80% 2 for steps; (j) Burgess salt, THF, reflux; (k) BrCCl3, DBU, CH2Cl2, 0 to 23 °C, 62% for 2 steps