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. Author manuscript; available in PMC: 2016 Mar 24.
Published in final edited form as: Nat Prod Rep. 2015 Feb;32(2):328–347. doi: 10.1039/c4np00051j

Scheme 17.

Scheme 17

Reagents and conditions (a) LiAlH4, THF, 0 °C; (b) NaH, BnBr, DMF/THF, 0 °C (77%, 2 steps); (c) 121, (COCl)2, CH2Cl2, rt; 120, DMF, rt (70%); (d) Et2NH, CH2Cl2, rt; (e) Boc2O, EtOH/CH2Cl2, rt; (f) Dowex 50W–X8, MeOH (90%); (g) TBAF, THF, rt (95%); (h) Swern Oxidation; (i) TFA, anisole, CH2Cl2, rt (72%, 128 : 129 = 0.72 : 1); (j) TrocCl, pyridine, CH2Cl2, 0 °C; (k) BnBr, K2CO3, TBAI, acetone, rt (85%, 2 steps); (l) Pd(PPh3)4, pyrrolidine, CH2Cl2, rt; (m) MOMBr, DIPEA, CH2Cl2, rt (56%, 2 steps); (n) DMDO; (o) NaBH3CN.