Remembering organic chemistry legend Robert Burns Woodward | April 10, 2017 Issue – Vol. 95 Issue 15 | Chemical & Engineering News

April 28, 2017

Organic chemistry legend…#Woodward
http://CEN.acs.org/articles/95/i15/Remembering-organic-chemistry-legend-Robert-Burns-Woodward.html Well illustrates cleverness in synthesis, eg porphyrin analogy for chlorophyll

QT:{{”
“Woodward’s work was less about inventing reactions, although he did do that on occasion. He didn’t, for example, design a reaction and then apply it over and over again to many natural products, a strategy that became common after Woodward’s death,

Woodward’s synthesis of the once popular antihypertensive drug reserpine, published in 1956, is one that many chemists point to as a highlight in the history of total synthesis of natural products. “It was founded on visionary ideas and published right about the time organic chemists were worrying about how to utilize the principles of conformational analysis in synthesis design,” Sorensen says. Woodward built reserpine’s intricate structure using simple reagents. At the end of the synthesis, he and his group corrected an errant
stereocenter by forcing an intermediate compound into an unfavorable conformation so that it epimerized into the correct stereoisomer. …
Sorensen points to Woodward’s synthesis of chlorophyll, which took four years to complete and was published in 1960, as a prime example of strategic risk taking in organic synthesis. Woodward thought the molecular architecture that defines the chlorins—a structural family that includes chlorophyll—might originate from a highly substituted porphyrin with a crowded periphery because of structural similarities, Sorensen explains.”
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Remembering organic chemistry legend Robert Burns Woodward | April 10, 2017 Issue – Vol. 95 Issue 15 | Chemical & Engineering News

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