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. Author manuscript; available in PMC: 2017 Jul 7.
Published in final edited form as: Org Biomol Chem. 2016 May 24;14(25):5894–5913. doi: 10.1039/c6ob00878j

Scheme 7.

Scheme 7

(−)-cis Clavicipitic acid. Reagents and conditions: (a) 82 (3 equiv.), K2CO3 (2 equiv.), DMF, room temperature, 3.5 h, 83%; (b) [Ir(cod)2]BARF (10 mol%), rac-BINAP (10 mol%), PhCl, 135 °C, 15 h, 79%; (c) HBr/ AcOH (10 equiv.), room temperature, overnight; (d) NaBH(OAc)3, (4.2 equiv.), Et3N, CH2Cl2, room temperature, 24 h, 53% (2 steps); (d) KOH, MeOH/H2O (2:1), room temperature, 15 min (ref [46])