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. Author manuscript; available in PMC: 2011 Jul 21.
Published in final edited form as: J Am Chem Soc. 2010 Jul 21;132(28):9567–9569. doi: 10.1021/ja1035495

Scheme 2.

Scheme 2

Synthesis of 6 En Route to Aplykurodinone-1 (1).

aKey: (a) MeLi, DME/THF, −50 °C; TFA, CHCl3, reflux, 73%; (b) HSCH2CH2SH, AcOH, p-TSA, 74%; (c) NaBH4, CH2Cl2/MeOH, −78 °C→ −40 °C; (d) MOMCl, iPr2NEt, CH2Cl2, 84% over 2 steps; (e) DIBAL-H, CH2Cl2, −78 °C; (f) Tl(NO3)3, MeOH/THF/H2O, 95% over 2 steps; (g) TsNHN=CHCOCl, PhNMe2, Et3N, CH2Cl2, 0 °C, 88%; (h) bis-(N-t-butylsalicylaldiminato) copper (II), PhMe, reflux, 40%; (i) NaBH4, CeCl3•7H2O; (j) I2, PPh3, imidazole, PhMe, reflux, 78% over 2 steps; (k) SmI2, THF/MeOH, 85%; (l) HCl, THF/H2O; (m) DMP, CH2Cl2, 80% over 2 steps.