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. Author manuscript; available in PMC: 2017 Apr 4.
Published in final edited form as: Chemistry. 2017 Feb 3;23(18):4327–4335. doi: 10.1002/chem.201604795

Scheme 1.

Scheme 1

Summary of ring distortion from 1. Reagents and Conditions: a) BrCN (3.0 eq.), DMF, μw, 100°C, 2.75 min, 45%; b) BrCN (3.0 eq.), ROH:CHCl3 (3:1), rt, 16 h, 14 – 63% (11 examples); c) Copper(I) Iodide (0.35 eq.), K2CO3 (1.5 eq.), DMEDA (0.7 eq.), MeCN, μw, 160 °C, 13 min, 70 – 73%; d) NCS (1.1 eq.), CH2Cl2, −41 °C, 0.75 h, crude; e) 0.5 M NaOMe/MeOH, rt, 2.5 h, 66%; f) 10% TFA (aq), reflux, 1 h, 58%; g) BrCN (3.0 eq.), DMF, rt to 60 °C, 22 h, 52%. Notes: DMEDA = N,N′-dimethylethylenediamine, NCS = N-chlorosuccinimide. *Indicates combined percent yield and isolated yields of ether diastereomers.