Dead Ends and Detours
Direct Ways to Successful Total Synthesis
M.A. Sierra, M.C. de la Torre
Wiley-VCH, 2004, 276 pages
Every chemist knows what is meant by the phrase,
"after some experimentation", as in "after some experimentation,
compound 665 was converted into compound 666
with 32% yield." More often than not, this means that the chemist
probably struggled for six months and lost his
graduate students and half of his remaining hair trying to get
the reaction to work. A lot of insight can be gained by learning
why some reactions don't work as expected and how the world's top
organic chemists solved the problem. This book describes 34 difficult
organic syntheses taken from the literature, of natural products
such as (+)taxusin, (-)strychnine, calphostin A, and the complex
macrolide cytovaricin, and the unexpected problems that were
encountered in their synthesis.
The treatment of each synthesis scheme as a sort of chemical chess
game against nature makes the subject more interesting than the usual
impersonal recitation of reagents and reaction conditions that would
be found in the original JACS articles. The authors also discuss
the more interesting key reagents that were sometimes needed, such
as the use of the exotic tetra-N-propylammonium perruthenate (TPAP)
to perform a simple alcohol oxidation. This book requires a solid
background in organic chemistry. It also has many (mostly minor)
typographical errors and misspellings, and a few nonsensical
sentences, caused by the Spanish authors' imperfect grasp of
English.
November 12, 2005Back
