While the carbonyl group is a very common starting point for bond disconnections in retrosynthetic analysis, an olefinic or acetylenic unit is also a useful reference point in many instances.
ACETYLIDE NUCLEOPHILES
While
the carbonyl group is a very common starting point for bond disconnections in
retrosynthetic analysis, an olefinic or acetylenic unit is also a useful
reference point in many instances. This is because a terminal acetylene can be
used as an effective nucleophile to install the triple bond into molecules and
it can be reduced stereospecifically to either the cis or trans olefin. Thus
for the cis-olefin target T, the
following retrosynthetic analysis leads to an efficient synthetic pathway which
uses a nucleophilic displacement by an acetylide anion as a key carbon–carbon
bond-forming step.
The
synthetic sequence would be
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