Syntheses of hormones such as estrone and the prostaglandins are but a few of Corey's innumerable achievements that have accelerated medical research. In fact, Corey says, organic chemistry's relevance to medicine was what hooked him on chemistry in the first place.
There has not been another book that has attempted to present a comprehensive, logical approach for stereoselective syntheses of stereochemically complex compounds. Certainly, many attempts have been made. However, the sheer number of tools one would need to master in order to present a blueprint for an approach has made this undertaking rather unwieldy. To make the logic of stereoselective analysis as accessible as possible, the book approaches it from the bottom up with three sections, each focusing on a different aspect of the synthesis problem.
Logic of Chemical Synthesis (Corey 1989) : Free …
The title of the paper is “Stereocontrolled organocatalytic synthesis of prostaglandin PGF2a in seven steps” but gave “the product in just six steps”?
In the last step the phosphonium is one carbon short, and how can a 47% yield give 1.9 g of a lower-MW (lost the heavy TBS) product starting from only 1.4 g?
A couple of the sentences in the optimization paragraph are backwards. Normally you’s expect the 2nd aldol to be in favor of the intramolecular reaction and the second catalyst could not be present at the same time.
The Logic of Chemical Synthesis (1st Ed.) by Corey, Corey & Cheng
Until he turned 70, Corey taught an organic synthesis course, Chemistry 115. He prepared meticulously for the lectures, wanting them to be as good as they could be. Except for one time when he was severely ill after a trip overseas, he never missed a class, not even on the day that he learned of his Nobel Prize.
The Logic of Chemical Synthesis. E. J. Corey and Xue …
Corey achieved the first synthesis of prostaglandin F2a in 1969 in 17 steps; which wasn't a bad benchmark for the year and the target! He then spent a lot of time improving on his first generation route, and it’s interesting to read his follow up papers for this purpose. In fact, despite a few flaws, Corey’s work actually became the basis of the 20-step commercial route used by Pfizer for commercial production of Latanoprost. I had Corey's original route drawn up for something else, so I've included it below.
The Logic of Chemical Synthesis by E.J
Corey's funding now comes exclusively from private sources. A major supporter is Pfizer, the pharmaceutical company that he has been advising since the 1950s. Because of the imperatives of confidentiality, the world may never know what new drug discovery programs, or indeed new lifesaving drugs, are the fruits of Corey's advice. What's clear is that, in advising what is now the world's largest pharmaceutical company, Corey goes far beyond the challenges of synthesis.
The Logic of Chemical Synthesis by E
"IN MY OWN RESEARCH, I always strive to do things that are useful to other people," Corey says. As an example, he pulls out a slide outlining a concise synthesis of the hormone estrone in which the key step is a Diels-Alder reaction catalyzed by a "little molecule that I'm just so proud of and excited about." Since 1938, it had been thought that an enantioselective Diels-Alder reaction of what is known as Dane's diene would efficiently yield the required ring system. People tried and failed, Corey says.