Email your assignment to me.
· List
and draw exact structures and reactions of the closest precedent to
your
proposed synthetic operations for every step you reference. I will take off points for steps for which
there is no
literature reference for key steps. Do not cite text books! Do not
cite Wikipedia
or other web resident knowledge. You may use this information, but you
will have to look up the original literature.
· Document your work by drawing structures and explaining the
closest precedent to your proposed work (not the whole paper/
reference). Don't make it
difficult for
the grader to conclude that someone can do the synthesis. Do not make
the grader have to hunt.
HINT1: The first thing you need to
do is build ball and stick models of both molecules. Now break bonds
one at a time, then two at a time. Think about ways to construct these
bonds. Think about which bonds are most labile. Think about
substructures searches that you can do on the molecules that you create
by disconnecting the structures. Think about the strategic nature of
preserving certain cycles. See Session 12.
HINT2: Start now. You might be
thinking that you have time to put this off; you don't.
{25 pts}
Analyze the two structures 3A
and 3B retrosynthetically.
Based on principles of molecular complexity make an argument about
which molecule is more difficult to synthesize. You will not be graded
on your opinion--there may not be a right or a wrong answer here. There
are many ways be convincing; there are many more ways to fail to
convince. If you are confident that both structures will fall to the
maquinations of your nimble mental faculties you may argue that point
also.
{75
pts.} Show your best route to your chosen target
molecule. Here is the place to include a lot of documentation. If you
are
trying to do this assignment without reading and considering the
assigned material, you are probably doubling your effort and time. You
should mine the literature for polycyclic compounds. You should read
the syntheses cited for longifolene.
The format for this problem can be
found on the web at: