Stereospecific Synthesis of 2,3‐Dimethoxy‐naphtho[1,2‐b]indolizidine

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Abstract
(11aS)‐ and (11aR)‐2,3‐dimethoxy‐naphtho[1,2‐b]indolizidine (9a and 9b) were synthesized from optically pure L‐ and D‐glutamic acid through several steps (scheme 1). All the intermediates of the route to the optical antipodes of 9 exhibit identical physical and spectral properties except the sign of the optical rotation values. The optical purity of the enantiomers of 6 was checked by 1H‐NMR spectra using Eu(tfc)3, that of the enantiomers of 9 by HPLC‐separation on a chiral column; the amount of racemization was less than 3% in 9a and 9b, respectively.