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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 5.

Scheme 5

(−)-Aurantioclavine (2). Reagents and conditions: (a) n-BuLi, DMF, THF, −78°C, 70%; (b) vinyl magnesium bromide, THF, −78°C, 5 min, 85%; (c) 73 (21 mol%), [{Ir(cod)Cl}2] (4 mol%), Sc(OTf)3 (20 mol%), DCE, 86% yield (93% ee); (d) AD-mix-α, t-BuOH/ H2O, room temperature, 5 d (e) NaIO4, MeOH/ H2O, 0 °C, 5 min; (f) LiHMDS, tetrazole 75, THF, −78 °C, 70% BRSM (3 steps); (g) TMSOTf, lutidine, CH2Cl2, 90%; (h) K2CO3, MeOH/ H2O, 100 °C, 90%.