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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 4. Synthesis of ent-cryptocaryol A and B (30a/b).

Scheme 4

Reagents and conditions: a) TBSCl, imidazole, DMF, 96%; b) DIBALH, CH2Cl2, −78 °C, 90%; c) (R,R)-Leighton, Sc(OTf)3 (5 mol %), CH2Cl2, −10 °C, 95%; d) acrylic acid, DCC, DMAP, CH2Cl2, 64%; e) Grubbs I (5–10 mol %), CH2Cl2, reflux, 87% or 78%; f) AcOH/H2O (4:1), 80 °C, 77% or 75%; g) TBAF, THF, 91%; h) Ac2O, Et3N, DMAP, CH2Cl2, 0 °C, 96%.