The oxa-Pictet�Spengler (OPS) reaction is a useful, relatively under-explored cyclisation reaction that efficiently produces natural and synthetic oxacyclic molecules. These molecules, which have useful properties for the treatment of cancer, tuberculosis or neurological disorders, are often chiral. The chirality of these molecules has a profound effect on their bioactivity. The OPS reaction often produces stereogenic centres, but examples of enantioselective OPS reactions are scarce and only moderately selective. The development of an efficient catalytic enantioselective reaction would enable expedient delivery of oxacylic bioactives.This work describes the syntheses of novel thieno-pyran anti-tubercular agents and research towards an enantioselective OPS transformation. The novel molecules were constructed using an OPS reaction as the key transformation. Efforts towards an enantioselective OPS reaction included the development of a Br�nsted acid-catalysed protocol and the discovery of a tandem Lewis acid-catalysed transformation translatable to a selective reaction.In this context, the term 'open science' refers to the practice of conducting research entirely in the public domain through a completely transparent process. Development of the OPS reaction was carried out using open science methodology, which was enabled through the use of an online electronic laboratory notebook and promotion of the science using popular social media platforms. This approach is currently being employed in drug discovery and the application of chemical methodology related to the OPS reaction.

Open science development of the catalytic oxa-Pictet-Spengler reaction

248th National Meeting (2014)

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