Book Review

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, 2005 Back