evolved highly sophisticated machinery for organic synthesis, many of which
resemble molecular assembly-line processes. So far chemists have been able to
apply this type of approach in the synthesis of peptides and oligonucleotides
but in these reactions, simple amide (C‒N) or phosphate (P‒O) bonds are
created. It is much more difficult to make C‒C bonds but this is central to the
discipline of organic synthesis. This difficulty is why organic synthesis is
challenging and why robust, iterative or automated methodologies have not yet
describe the application of iterative homologation of boronic esters using
chiral lithiated carbamates and chloromethyllithium enabling us to grow carbon chains
with control over both relative and absolute stereochemistry. Applications of
this strategy to the synthesis of natural products will be demonstrated. In
addition, the methodology is used to answer fundamental questions about nature
and the specific role of methyl substituents in carbon chains. By understanding
their role, I will show that molecules can be created with linear or helical
conformations or hybrids of the two.
and tertiary boronic esters are versatile intermediates and can be transformed
into alcohols, alkenes, and amines. I will show how this can be expanded to
include new coupling reactions with a broad range of aromatics, and also new
reactions that convert the boronic ester moiety into a host of other functional
groups with full stereocontrol.5
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Balieu, G. E. Hallett, M. Burns, T. Bootwicha, J. Studley, V. K. Aggarwal, J.
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M. Burns, S. Essafi, J. R. Bame, S. P. Bull, M. P.
Webster, S. Balieu, J. W. Dale, C. P. Butts, J. N. Harvey, V. K. Aggarwal, Nature, 2014, 513, 183.
Wu, P. Lorenzo, S. Zhong, M. Ali, C. P. Butts, E. L. Myers, V. K. Aggarwal, Nature, 2017, 547, 436.
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2017, 53, 5481.