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Scripps Research team wins global race to achieve landmark synthesis of perplexing natural product
Date:1/12/2010

ever since he arrived at Scripps Research as a faculty member more than six years ago. During that time, the group developed techniques to synthesize several compounds related to Palau'amine, but the ultimate goal remained elusive. Numerous attempts, however, added important information and techniques that would ultimately prove critical.

The Quest Heats Up

Increasingly desperate and working with handheld molecular models, Baran and his team eventually hit on the idea of a molecule dubbed macro-Palau'amine that he felt his group could create. If so, he became convinced it could be transformed into Palau'amine. As work to create macro-Palau'amine heated up, graduate students, including the new paper�s first authors graduate student Ian Seiple and Research Associate Shun Su, Ph.D., would eventually set up a cot in the laboratory and begin to work around the clock.

"It was the Scripps Hilton for a long time," says Baran, "and when it was finally done we were all elated, as you might imagine."

The group's earlier trials produced intermediate compounds that took them part of the way to Palau'amine, but there was still much to do. One of the most significant later advances that allowed them to succeed was the invention of an oxidation reaction helped along by silver. The reaction could place an essential group of oxygen and hydrogen atoms known as a hydroxyl at a particular spot on an emerging molecule with seemingly laser-guided precision. The reagent that the Scripps Research team developed for this purpose, silver picolinate, has now been commercialized by Aldrich.

"The technique had no precedent, but we knew that if it could be invented it would dramatically simplify everything," says Baran�and it did.

This silver-mediated oxidation stabilized an intermediate molecule enough to allow five final steps to macro-Palau'amine. Once the team had that, the final transformation to Palau'amine proceede
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Contact: Keith McKeown
kmckeown@scripps.edu
858-784-8134
Scripps Research Institute
Source:Eurekalert

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