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. Author manuscript; available in PMC: 2015 Apr 29.
Published in final edited form as: Mol Imaging Biol. 2014 Dec;16(6):765–772. doi: 10.1007/s11307-014-0748-x

Scheme 3.

Scheme 3

Synthesis of precursor (−)-9. Reagents and conditions: a) Conc. HCl, 100 °C, 8 days, 96 %; b) 1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene, K2CO3, EtOH, reflux, 4 days, 62 %; c) BnBr, K2CO3, acetone, 45 °C, overnight, 62 %; d) Separation of enantiomers of 10 on HPLC: Chiralcel OD column 250×10 mm; mobile phase: 60 % isopropanol in hexanes; flow rate: 4.0 ml/min; (+)-enantiomer at 22 min and (−)-enantiomer at 49 min; e) (−)-10, 10 % Pd/C, MeOH, 70 psi, 21 h, 90 %.