Woodward, Robert Burns

(1917-1979)

Robert Burns Woodward was born on April 10, 1917, in Boston, Massachusetts. He is recognized by the worldwide scientific community as the leading figure of this century in organic chemistry. Wood­ward began his scientific career at the age of eight anc before becoming a teenager had already completed much of the experimental work that would normally be carried out in college. Indeed, when Woodward was a freshman at the Massachusetts Institute of Technology, he was given his own research labora­tory at the age of sixteen. In only four years he had graduated with both a bachelor's and doctor's de­gree. After a short stay at the University of Illinois, Woodward returned to Cambridge, Massachusetts, and to Harvard University, where he was to spend the rest of his life and his career. Chemists have made contributions of monumental

proportions to humankind's progress in the past two centuries. In 1838 WOHLER and LIEBIG, two leading chemists of their time, stated, "the philoso­phy of chemistry will draw the conclusion that the synthesis of all organic compounds, as long as they are not part of an organism, must be seen as not merely probable but certain." This prediction was admirably fulfilled by Woodward.

In 1944 at the age of twenty-seven, Woodward, then an assistant professor in the chemistry depart­ment at Harvard, succeeded in synthesizing quinine. Quinine, the most important antimalarial at the time, had not been available since the beginning of World War II. The research was supported by Edwin Land and the Polaroid Corporation of Cambridge, who sought to replace quinine, which they used as a polar­izer. Woodward's synthesis of quinine did not of it­self provide a commercial route to quinine. Rather, it completed the goal that generations of chemists had strived for since the 1850s and initiated the modern area of organic synthesis. His synthesis of quinine and the work that he performed on the then-miracle antibiotic penicillin established Woodward as the leader of what history may well look back and de­scribe as the "golden age" of organiC chemistry. Organic chemists plan their synthetic strategies

both forward, from readily available starting mate­rials, and backward, from their ultimate goal the fin­ished product. This exercise requires an intimate knowledge of the three-dimensional (3D) structure of each intermediate in the synthetic scheme and an un­derstanding and intuition of how 3D properties affect reactivity of molecules. Woodward was a master of these skills. Not only was he a key figure in most of the major events that directed organic chemistry dur-ing this century, but he was also a leader in the use c spectroscopic methods that chemists use to aid their exploration into the detailed structure of molecules. Early in his career he developed theories that related the structure of a molecule and the way in which it absorbs ultraviolet and visible light. He also helped

explain how the absorption of polarized light could be used to predict the 3D structure of molecules by his codevelopment of the octant rule. Woodward was a pioneer in the use of infrared and NUCLEAR MAG­NETIC RESONANCE spectroscopy, and helped estab­lish HIGH-PERFORMANCE LIQUID CHROMATOG­RAPHY (HPLC), which is still the most versatile method to separate complex mixtures into their indi­vidual components. Throughout his career Woodward focused his at­

tention on determining the structure of and synthesiz­ing molecules of biological importance. These achievements are too extensive to list in detail but include molecules such as strychnine, antibiotics, cholesterol, cortisone, lysergic acid, ferrocene, reser­pine, tetracyclines, and chlorophyll. This work re­sulted in 1965 in the award of the Nobel Prize in chemistry to Woodward for "contributions to the art of organic synthesis." Woodward's most spectac­ular and difficult synthesis was that of nature's most complex nonpolymeric molecule, vitamin BI\. Wood­ward and his colleague Albert Eschenmoser com­pleted the synthesis in 1976; the experimental work involved more than one hundred chemists from twenty nations.

During the early steps of the vitamin B12 synthesis Woodward was surprised and no doubt dismayed that the predicted outcome of one of his reactions was wrong. Woodward never allowed the complexi­ties of nature to daunt him. Indeed, he always inter­preted the message that nature gave him and used this knowledge to achieve his goals. B12 provides the par­adigm for this, since this one reaction that had the audacity to defy and confuse him resulted in a collab­oration with Roald Hoffmann (who was awarded the Nobel Prize in 1981 for this work). Together they developed a set of theoretical rules, using MOLECU­LAR ORBITAL THEORY to explain what, at the time, as viewed as a wide range of (apparently) unrelated organic reactions, and to predict many others. In­deed, so powerful and all-encompassing are the Woodward-Hoffmann rules that when Woodward and Hoffmann considered violations of these rules they concluded, "there are none." Woodward died in Cambridge on July 8, 1979, at

the age of sixty-two. However, he slept for only three hours a day the whole of his adult life, so even in his

relatively short life he spent more hours awake than the average person who lives to be one hundred.

BIBLIOGRAPHY

BOWDON, 1\11. E.; BENFEY, T. Robert Burns Woodward and the Art of Organic Synthesis; Philadelphia:

Chemical Heritage Foundation, 1992.

DAVID DOLPHIN