Applications of domino transformations in organic synthesis by Scott A., Prof. Snyder, Marco Bella, Alexander Dömling, Jon

By Scott A., Prof. Snyder, Marco Bella, Alexander Dömling, Jon Boyce, Gaelle Blond, Iain Coldham

The swift speed of evolution in domino, or cascade-based alterations has revolutionized the perform of chemical synthesis for the construction of average items, designed molecules, and pharmaceuticals.


"Science of Synthesis: functions of Domino variations in natural Synthesis" explores the subject completely and systematically, serving because the foundation for useful functions and destiny study. The 2-volume set offers the state-of-the-art when it comes to layout, technique, and experimental systems, resulting in a number of occasions being complete inside a unmarried response vessel. The content material is geared up by way of the center form of response used to start up the development, be it a pericyclic response, a metal-mediated transformation, radical chemistry, or an acid-induced cascade between many others.


Volume 2 covers pericyclic reactions (Diels-Alder, sigmatropic shifts, ene reactions), dearomatizations, and additions to C-O/C-N a number of bonds.

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50 equiv) and the mixture was heated under microwave irradiation at 170 8C for 8 h. After cooling to rt, the solvent was evaporated. 48 g (74%). 2 Through Benzyne Formation Since their correct identification by Roberts in 1953,[60] benzynes have enjoyed a privileged position in the execution of concise molecule synthesis. Benzynes can be regarded as exceptionally labile intermediates and, as a result, are almost universally generated in situ, making them well suited to application in domino processes.

1 The Diels–Alder Cycloaddition Reaction in the Context of Domino Processes J. G. West and E. J. Sorensen General Introduction The title that Otto Diels and Kurt Alder chose for their 1928 publication, “Syntheses in the Hydroaromatic Series”, in Annalen[1] did not signal the revolution that their new insights would bring to the field of organic chemistry. ” The very next sentence, “We explicitly reserve for ourselves the application of the reaction discovered by us to the solution of such problems”, is even more colorful, but, in reality, nearly a quarter of a century would pass before the power of the “Diels–Alder” reaction was demonstrated in the context of natural product synthesis.

The clear soln was concentrated by passing a stream of dry N2 over it for 10 min. 0 mg. The crude bisimine was taken up in AcOH (1 mL) and placed in an 80 8C oil bath for 11 h. After cooling to 0 8C, the mixture was partitioned between CH2Cl2 (5 mL) and 2 M NaOH (5 mL) and stirred vigorously for 15 min. The layers were separated, and the aqueous phase was extracted with three portions of CH2Cl2. The combined organic phases were washed with brine and dried (MgSO4). 2 mg (65%). 3 Through Deprotonation of an Alkene A keen insight from Danishefsky[29] and co-workers has been reported in the construction of the anthraquinone fragment of enediyne antibiotic dynemicin A.

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