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. Author manuscript; available in PMC: 2014 Jun 26.
Published in final edited form as: J Am Chem Soc. 2013 Jun 14;135(25):9334–9337. doi: 10.1021/ja404401f

Scheme 5. Synthesis of cryptocaryol A and B (9 and 10).

Scheme 5

Reagents and conditions: a) DIBALH, CH2Cl2, −78 °C, 90%; b) 1-pentadecyne, n-BuLi, THF, −78 °C; c) Dess–Martin periodinane, CH2Cl2, 0 °C, 68 % (2 steps); d) (R,R)-Noyori (5 mol %), Et3N, HCO2H, 98%; e) NBSH, Et3N, CH2Cl2, 98%; f) TBSCl, imidazole, DMF, 94%; g) DDQ, CH2Cl2, H2O, 0 °C, 92%; h) Dess-Martin periodinane, CH2Cl2, 0 °C, 62%; i) (S,S)-Leighton, Sc(OTf)3 (5 mol %), CH2Cl2, −10 °C, 95%; j) acrylic acid, DCC, DMAP, CH2Cl2, 80%; k) Grubbs I (5–10 mol %), CH2Cl2, reflux, 76% or 70%; l) AcOH/H2O (4:1), 80 °C, 70%; m) TBAF, THF, 92%; n) Ac2O, Et3N, DMAP, CH2Cl2, 0 °C, 72%.