Total Synthesis of (+)-Oxo-tomaymycin,Organic Process Research & Development

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Total Synthesis of (+)-Oxo-tomaymycin
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2020-02-10 , DOI: 10.1021/acs.oprd.0c00009
Françoise Benedetti , Marc-Antoine Perrin , Sebastien Bosc ₁ , Franck Chouteau ₁ , Nicolas Champion ₁ , Antony Bigot

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(+)-Oxo-tomaymycin, a naturally occurring substance of the pyrrolo-1,4-benzodiazepine family, was synthesized using a short and efficient route. The key construction of the seven-membered ring by amide bond formation was realized via a chemoselective Ar-NO₂ reduction using TiCl₃ under acidic conditions, followed by a spontaneous cyclization. This synthesis was easily scaled up to 80 g, and it should be amenable to the production of larger quantities.

中文翻译：

（+）-Oxo-tomaymycin的全合成

（+）-Oxo-tomaymycin，吡咯并-1,4-苯并二氮杂family家族的天然物质，是使用一种短而有效的途径合成的。通过在酸性条件下使用TiCl ₃进行化学选择性的Ar-NO ₂还原，然后进行自发环化，可实现通过酰胺键形成七元环的关键结构。该合成很容易按比例放大到80 g，应该适合于大量生产。

更新日期：2020-02-10

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