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Thermal rearrangement of cyclopropyl imines. : II. Synthesis of a mesembrine model

✍ Scribed by R.V. Stevens; Mark P. Wentland

Publisher: Elsevier Science
Year: 1968
Tongue: French
Weight: 121 KB
Volume: 9
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)89656-2

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✦ Synopsis

We recently reported (3) the total synthesis of the simple pyridine alkaloids myosmine [3] and apoferrorosamine [4] by means of the thermally induced, acid catalyzed, rearrangement of cyclopropyl ketimines [l]. The success and efficiency of these experiments has prompted us to further investigate the crucial rearrangement step, [l] to [2], as a general method of alkaloid synthesis. We wish now to report the synthesis of a model [5, R = H] of the Amarvllidaceae alkaloid mesembrine [5, R = OCH3].

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