Who he was
Robert Burns Woodward was a child prodigy from Boston who taught himself chemistry at home, entered MIT at 16 and earned his PhD at 20. He spent his whole career at Harvard. He was famous for long lectures drawn in coloured chalk, for working late into the night and for always wearing a blue tie.
Key contributions
Total synthesis. Many medicines and natural pigments are large molecules with several rings and many stereocentres. Total synthesis means building such a molecule from simple starting materials, one reaction at a time, with every step and every 3D arrangement under control. Woodward showed that this was possible even for the most complex molecules of nature: quinine (1944), cholesterol and cortisone (1951), strychnine (1954), chlorophyll (1960) and, with Albert Eschenmoser, vitamin B12 (1972).
Thinking before mixing. Woodward planned each synthesis on paper using reaction mechanisms, predicting which bonds would form and with what stereochemistry, rather than relying on trial and error. This way of reasoning is how organic chemistry is taught today.
Key idea
A synthesis is a chain of reactions, and the overall yield is the product of the yields of every step. Ten steps at 80 % each give only about 11 % overall, which is why Woodward’s long syntheses needed such careful planning.
Rules from light and orbitals. In 1941 he showed that the ultraviolet absorption of a molecule can be predicted from its structure, making UV spectroscopy a tool for finding structures. In 1965, with Roald Hoffmann, he formulated the Woodward–Hoffmann rules, which use the symmetry of molecular orbitals to predict whether certain ring-forming reactions happen with heat or with light. Hoffmann shared the 1981 Nobel Prize for this work; Woodward had died in 1979, and Nobel Prizes are not awarded after death.
Prizes and legacy
He won the 1965 Nobel Prize in Chemistry “for his outstanding achievements in the art of organic synthesis”. Many of the leading synthetic chemists of the next generation trained in his laboratory, and his strategies are still followed in the making of new medicines.
Connections to your lessons
His work builds on the lessons on functional groups and organic reactions, and his UV rules connect to the Beer–Lambert law, which links light absorption to concentration. His synthesis of quinine links to the quinine story in Explore.
Timeline
- 1917Born in Boston; as a child he works through a college chemistry textbook in a home laboratory.
- 1937Earns his PhD at MIT aged 20, two years after entering at 16, and joins Harvard, where he stays for his whole career.
- 1941Publishes rules that predict the ultraviolet absorption of organic molecules from their structure (the Woodward rules).
- 1944With William Doering, completes a formal synthesis of quinine, the antimalarial drug, front-page news during the Second World War.
- 1951Completes the syntheses of cholesterol and cortisone.
- 1954Synthesizes strychnine, a molecule with seven interlocking rings.
- 1960Synthesizes chlorophyll, the green pigment of plants.
- 1965Awarded the Nobel Prize in Chemistry. With Roald Hoffmann, publishes the Woodward–Hoffmann rules, which predict the outcome of a whole family of reactions.
- 1972With Albert Eschenmoser and about 100 co-workers, completes the synthesis of vitamin B12 after more than ten years.
- 1979Dies in Cambridge, Massachusetts, while working on the antibiotic erythromycin.
Sources and further reading
Explore next
1820 Quinine isolated from cinchona bark
Quinine: The Gift of the Cinchona Tree
The bark that treated malaria for 300 years, and the failed synthesis that started the chemical industry.
Cinchona bark from the Andes, the isolation of quinine in 1820, Perkin's accidental discovery of the first synthetic dye in 1856, the long road to its synthesis, and why tonic water glows.
Dorothy Crowfoot Hodgkin
1910–1994
Dorothy Hodgkin (1910–1994) used X-ray crystallography to solve the structures of penicillin, vitamin B12 and insulin, and won the 1964 Nobel Prize in Chemistry.
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