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. Author manuscript; available in PMC: 2018 Apr 17.
Published in final edited form as: J Am Chem Soc. 2016 Oct 17;138(42):13794–13797. doi: 10.1021/jacs.6b07731

Scheme 2.

Scheme 2

Lanicemine (AZD6765) and Preparation of All Four Stereoisomers of ‘β-Fluoro-Lanicemine’ (8).

Reaction conditions: a) Bu3SnH (4 equiv.), AIBN (0.4 equiv), benzene, 80 °C, 180 min (dr ≈ 2:1 anti:syn, 74%); b) TFA, CH2Cl2, 180 min (98%). In each case, diastereomers 8 were purified by reverse phase preparatory HPLC as their TFA salt adducts (see SI). Enantiomeric excess (ee) for stereoisomers 8 follow from ee of 7f/ent-7f.