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Synthesis of the Preininger-Alkaloid and its Enantioselective Reduction to Macrostomine
Mahboobi, Siavosh and Wiegrebe, Wolfgang (1991) Synthesis of the Preininger-Alkaloid and its Enantioselective Reduction to Macrostomine. Archiv der Pharmazie 324, pp. 275-281.Date of publication of this fulltext: 08 Jul 2010 05:06
Article
DOI to cite this document: 10.5283/epub.15724
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 ...
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 of 2b with a modified Iwakuma-reagent
followed by N-formylation and subsequent LiAlH4-reduction produced (R)-
(+)-macrostomine (enantiomer of 1) in 72 % optical purity.
Das Preininger-Alkaloid (Dehydro-normacrostomin, 2b, Scheme 1) wurde
ausgehend von rac. α-Acetyl-3,4-dimethoxybenzylcyanid (3) über die
Schlüsselverbindung 4-Acetyl-6,7-dimethoxy-1 -(3,4-methylendioxybenzyl)
isochinolin (11) synthetisiert. Die Umsetzung von 11 über eine Mannich-
Base zum Nitril 17 (Scheme 7) und dessen schonende Hydrierung führten
zum Preininger-Alkaloid (2b). - Die Reduktion von 2b mit einem modifizierten
Iwokuma-Reagenz, N-Formylierung und Alanat-Reduktion lieferten
(R)-(+)-Macrostomin (Enantiomer von 1) in 72 proz. optischer Reinheit
Involved Institutions
Details
| Item type | Article |
| Journal or Publication Title | Archiv der Pharmazie |
| Publisher: | John Wiley & Sons |
|---|---|
| Volume: | 324 |
| Page Range: | pp. 275-281 |
| Date | 1991 |
| Institutions | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe |
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences |
| Status | Published |
| Refereed | Yes, this version has been refereed |
| Created at the University of Regensburg | Unknown |
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-157246 |
| Item ID | 15724 |
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