I spotted a couple of interesting reviews recently, one with the intriguing title of “Discovery of Novel Synthetic Methodologies and Reagents during Natural Product Synthesis in the Post-Palytoxin Era“, this one by Schindler etal from the university of Michigan at Ann Arbor. and appears in Chemical Reviews.
Now palytoxin was isolated quite some time ago and Kishi synthesised it in 1989, discovering the well known Nozaki-Hiyama-Kishi reaction, which has in the intervening period been much refined. Well in the 20 or so years organic chemistry has advanced at a tremendous rate. Just look at the power of catalysis these days or cross-coupling or indeed metathesis processes. But probably the best area is the activation and functionalisation of C-H bonds. Or the discovery of a novel reagent to do reaction X to Y. Hardly a day goes by without one of these themes appearing in one journal or another. Schindler provides us with some interesting examples of some of these reactions and reagents and this is a review to be recommended.
The other review by Shenvi presents alkaloid synthesis. He identified about 5 different strategies to alkaloid synthesis based upon the key step. In the table of contents he actually presents 6; reduction, Mannich/Cascades, radical amination, pericyclic reactions and hydroamination. Following through with examples of alkaloid synthesis he highlights these reaction types and then proceeds to discuss individual total synthesis. The section on alkene hydroamination is of particular interest. The message is really “If a single, take-home message can be extracted from this survey, it is the importance of minimizing the addition of extraneous functional groups and especially their interconversions within a synthetic sequence, and instead utilizing chemoselective reactions of functionality present in both feedstock starting materials and the target.“
So two good reviews for bedtime reading, helps as a sleep aid.
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