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. Author manuscript; available in PMC: 2008 Sep 26.
Published in final edited form as: J Am Chem Soc. 2006 Nov 29;128(47):15084–15085. doi: 10.1021/ja065907x

Scheme 2. Completion of the synthesisa.

Scheme 2

a Conditons: (a) Ac2O, Py, 93%; (b) DDQ, pH 7 buffer, 79%; (c) Phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside S-Oxide, Tf2O, DTBMP, ADMB, propionitrile, −78 °C, 76%; (d) NH3 in IPA/ CH2Cl2; (e) ethylenediamine, EtOH, 60 °C (f) Ac2O, EtOH, (g) Ac2O, Py, 66% over 4 steps; (h) H2, Pd(OH)2/C, MeOH; (i) Ac2O, Py, 63% over 2 steps; (j) BF3·Et2O, CH2Cl2, 97%; (k) 2-amino-cyclopentane-1,3-dione, HATU, DIPEA, CH2Cl2/DMF, 55%; (l) NaOH, THF, 80%; (m) Ac2O, Py, 78%; (n) H2NNH2-HOAc, 53%; (o) i. 2-Chloro-1,3,2-benzodioxaphosphorin-4-one, 85%; ii. (R)-3-hydroxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]propanoate, 1-adamantanecarbonyl chloride, NMM/CCl4/Py/CH3CN/H2O (1:2.5:6:1:1), 62%; iii. 0.1 N LiOH, THF/H2O (1:1), then AcOH, 47%.18