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Synthesis of the Preininger-Alkaloid and its Enantioselective Reduction to Macrostomine

URN to cite this document:
urn:nbn:de:bvb:355-epub-157246
Mahboobi, Siavosh ; Wiegrebe, Wolfgang
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Date of publication of this fulltext: 08 Jul 2010 05:06


Abstract

The Preininger-alkaloid, dehydro-normacrostomine (2b, Scheme 1) was synthesized starting from rac. α-acetyl-3,4-dimethoxybenzylcyanide (3) (Scheme 2). The key intermediate 4-acetyl-6,7-dimethoxy-l-(3,4-methylenedioxybenzyl) isoquinoline (11) is converted via a Mannich base to the nitrile 17 (Scheme 7) which in turn is cyclized to the Preininger-alkaloid (2b) by careful hydrogenation. - Reduction ...

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