An Integrated Flow and Batch-Based Approach for the Synthesis of O-Methyl Siphonazole

Abstract

The bisoxazole containing natural product O-methyl siphonazole was assembled using a suite of microreactors via a flowbased approach in concert with traditional batch methods. The use of a toolbox of solid-supported scavengers and reagents to aid purification afforded the natural product in a total of nine steps.

The integration of flow reactors into synthetic organic chemistry

“…DAST has also found application in the cyclodehydration of β‐hydroxy amines which are efficiently converted to the corresponding oxazolines in excellent yields (Scheme ) . This has also allowed for the construction of a number of chiral PyBOX ligands in flow …”

“…130,132 This has also allowed for the construction of a number of chiral PyBOX ligands in flow. 133,134 Flow synthesis of novel chemical building blocks Access to a wide array of chemical building blocks is an essential perquisite for many medicinal chemistry synthesis programmes. These compounds can be simple core templates enabling rapid chemical decoration in initial hit finding screens or more specially tailored structures designed to enhance a certain physical characteristic or present a particular functional pattern wileyonlinelibrary.com/jctb Scheme 9.…”

Continuous flow reaction monitoring using an on‐line miniature mass spectrometer

“…[9] Although still considered to be in its infancy, the field of flow chemistry has progressed to the extent that total syntheses of natural products have been demonstrated. [10][11][12][13][14][15][16] Flow synthesis involves the serial manipulation of reactant streams using modular components such as mixers, temperaturecontrolled reactors, and packed columns. Peristaltic or piston pumps are generally used to maintain and meter the flow in meso-scale systems, whereas syringe pumps are used for micro-scale syntheses.…”

The route from problem to solution in multistep continuous flow synthesis of pharmaceutical compounds

“…70,104 The combination of multiple, differently functionalized scavenger resins is a common practice for the removal of several different impurities. 44,66,33,102,[105][106][107] In an illustrative example, removal of homogeneous transition metal complexes was possible this way ( Fig. 17), which prevented harmful catalytic activity in downstream heterogeneous nitro group reductions in the flow synthesis of the fungicide Boscalid Ò .…”