Organic Syntheses Database

Wiley/Organic Syntheses, Inc: 2003. http://www.interscience.wiley.com/db/os Available through a site licence.

The total synthesis of complex natural products remains one of the most tangible and often elegant demonstrations of the chemist's craft. Some practitioners have turned these endeavours into something approaching an art form. It is also often the only route by which quantities of rare compounds such as eleutherobin or bryostatins can be made available for biological evaluation. Any synthesis, whether of a rare, highly potent natural product or of a more mundane yet equally important intermediate for a prescription drug, requires the careful selection of starting materials and potential synthetic routes.

Synthetic chemists already have a number of information sources, including online search sites such as Crossfire Beilstein (http://www.beilstein.com) and the American Chemical Society's SciFinder (http://www.cas.org). There are also printed reference works such as Fieser's Reagents for Organic Synthesis (Wiley), Comprehensive Organic Synthesis (Pergamon, now Elsevier) and of course Organic Syntheses (Wiley).

Organic Syntheses is the 'Mrs Beeton' for synthetic chemists. If you can find a 'recipe' for the reaction or compound you wish to make in these volumes, you can guarantee that the chemistry will work, because each entry is checked for accuracy, safety and reliability. There is a cumulative index for the first 70 volumes, although many libraries do not have either this index or a complete set of 80 volumes. The release of the Organic Syntheses Database now provides access to all 80 on your computer screen.

So how does it perform? The user can search for structures and part-structures by importing these from one of their own drawing packages into a display box, and this is probably the most useful function. I tried several structures I wanted to synthesize and others that I knew to be within the volumes of Organic Syntheses, and obtained accurate links to the full text for all of them. Much less useful is the search for reaction types and named reactions. An enquiry about the aldol reaction elicited just one response, and no response was returned for queries on the Reformatsky and Heck reactions. Yet the term palladation produced two responses, both referring to syntheses submitted by Heck, and there are many others within the 80 volumes that have clearly been missed by this route.

Searches that use either keywords or author were generally very good, so searching for methodology associated with a key reagent, such as osmium tetroxide or palladium acetate, will elicit a large number of citations although, irritatingly, reaction names (Heck or Mitsunobu, for example) elicit nothing. The utility of the database is extended by the ability to search other Wiley databases, including EROS, the Encyclopaedia of Reagents for Organic Synthesis (although my login and password denied me access to explore these possibilities), and access to Organic Reactions will follow next spring.

Overall, the database is easy to use and will complement rather than replace the other existing online search tools. The one major advantage of the Organic Syntheses Database is that it provides access to an instant recipe that will work, rather than to a list of literature references in which the chemistry may or may not work.