Reissert—Pschorr sequence

Splendidine (37), a new oxoaporphine, has been obtained from Abuta rufescens Aublet ( = A. splendida) (Menispermaceae). Following its structural elucidation, its total synthesis was achieved via a Reissert-Pschorr sequence The known phenolic oxoaporphine subsessiline, found in a Guatteria species (Annonaceae), has been established to possess structure (39) instead of the... 

Imenine, an oxoaporphine oxygenated at C-4, has been synthesized by a Reissert-Pschorr sequence shown in Scheme 14.1. °... 

The synthesis of three l,2,10,ll-tetrasubstituted./V-(n-propyl)noraporphines, using either the Bischler-Napieralski-Pschorr sequence or a Reissert alkylation-Pschorr cyclization, has been achieved.29 Patents have been taken out on the morphine-apomorphine rearrangement that is induced by phosphoric acid and which leads to N- alkylated norapomorphines.30 Other patents concern the vanadium-trichloride-induced cyclization of tetrahydrobenzylisoquinolines that are hydroxylated at C-7, to furnish a series of 1-hydroxylated aporphines such as thaliphorphine. 31,32... 

The synthesis of three new racemic aporphines (22)—(24), using either a Bischler-Napieralski-Pschorr sequence or a Reissert-Pschorr route, has been described. ... 

The Reissert method15—conversion of an isoquinoline to a 2-benzoyl-1,2-dihydroisoquinaldonitrile (Reissert compound), alkylation, and hydrolysis—has enjoyed wide success in the synthesis of benzyliso-quinoline and related alkaloids.16,17 In particular, aporphines are prepared conveniently by converting isoquinolines to I-(o-nitrobcnzyl)-isoquinolines via a Reissert sequence, followed by A7-alkylation, reduction, and Pschorr cyclization.17... 

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