MAHBOOBI, S and WIEGREBE, W (1991) SYNTHESIS OF THE PREININGER-ALKALOID AND ITS ENANTIOSELECTIVE REDUCTION TO MACROSTOMINE. ARCHIV DER PHARMAZIE, 324 (5). pp. 275-281. ISSN 0365-6233,
Full text not available from this repository.Abstract
The Preininger-alkaloid, dehydro-normacrostomine (2b, Scheme 1) was synthesized starting from rac. alpha-acetyl-3,4-dimethoxybenzylcyanide (3) (Scheme 2). The key intermediate 4-acetyl-6,7-dimethoxy-1-(3,4-methylene-dioxybenzyl)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 of 2b with a modified Iwakuma-reagent, followed by N-formylation and subsequent LiA1H4-reduction produced (R)-(+)-macrostomine (enantiomer of 1) in 72 % optical purity.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ; |
| Depositing User: | Dr. Gernot Deinzer |
| Last Modified: | 19 Oct 2022 08:46 |
| URI: | https://pred.uni-regensburg.de/id/eprint/55009 |
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