OXYGEN
The following year at a Gordon Con ference, Robert B. Woodward from Har vard, Lewis H . Sarett from Merck, Gilbert Stork from Columbia, and I from CARL DJERASSI, STANFORD UNIVERSITY Syntex demonstrated the inherent collegiality of science by composing a spoof letters (C and H) becomes the steroid "Bible XYGEN IS A TRICKY SUBJECT TO under t h e authorship of F. Nathaniel of Life" through addition of a third letter, be offered on a silver platter. No Greene and AlvinaTurnbull titled "Partial O, that nature—and occasionally clever such platter is large enough to Synthesis of Cortisone from Neohampchemists—introduce into select places on cope with any but the smallest togenin" (a putative constituent morsels from the giant pantry of a potentially inexhaustible filled with oxygen-containing goodies. source: New Hampshire maple Rather different from an element with a syrup). Whereas our earlier, tes three-digit atomic number, where modest tosterone-drenched claims in hors d'oeuvres suffice. JACS had each trumpeted the One need not be a chemist to know that "first successful introduction of without oxygen a human life would cease in a C-ll oxygen function into a seconds or minutes rather than decades. But steroid devoid of functionality as an organic chemist who has practiced his in ring C," we now jointly pro art for more than halfa century I must con claimed "the first successful in cede that without oxygen I would not have troduction of a 3-keto group in published a single paper, because most of to an 11-oxygenated steroid my chemical life was spent grazing in steroid devoid of functional groups in pastures. Few classes of organic molecules ring A." are as interesting as steroids—covering the A C T I N G U P Scheele, Mme. Lavoisier, and gamut from sex hormones, oral contracep The subsequent 4 0 years of Priestley in "Oxygen" simulate Lavoisier's famous tives, bile acids, corticoids, vitamin D, and my research career featured a experiment on oxygen's role in respiration. cardiac glycosides to anabolic drugs oi shift from synthesis to the ap abuse—yet this panoply of biological di plication of physical methods. But even that template. I shall cite one example. versity is based on a single chemical tem here, steroids were the focus of all our stud Arguably the hottest topic in synthetic plate: the tetracyclic C 17 H 28 steroid skele ies and oxygen the key to our successes. If organic chemistry around 1950 was corti ton. A thin paperback written solely in twc it had not been for our choice of the carsone—the glamour steroid that had been bonyl function and its associat anointed with the 1950 Nobel ed strong Cotton effect, we nev Prize in Physiology or Medicine. OXYGEN AT A GLANCE er would have arrived at t h e Pictures of helpless arthritics generalizations derivable from dancing within days of cortisone Name: From the Greek oxygènes, acid administration flooded the me optical rotatory dispersion and forming. The name came from an india. The fierce competition was circular dichroism or drawn correct belief by Lavoisier that oxygen described in breathless prose by many mechanistic conclusions was needed to form all acids. Harper's Magazine in 1951: "The from the mass spectra of such Atomic mass: 15.99. new ways ofproducing cortisone oxygen-containing substrates. History: The discovery of oxygen is THIS ELEMENT come as the climax to an unre BROUGHT usually credited to English chemist But as a chemist turned play TO YOU BY strained, dramatic race involv Joseph Priestley in 1774. It was discovwright, let me end with some DOW CORNING ing a dozen of the largest Amer ered earlier by Carl W. Scheele in Upplines from "Oxygen"—a play I ican drug houses, several leading sala, Sweden, but published later. wrote with Roald Hoffmann: foreign pharmaceutical manufacturers, Occurrence: 0 2 makes up about ASTRID: First to the discovery: No one three governments, and more research per 20.95% of the atmosphere by volume. will question that oxygen confers great ben sonnel than have worked on any medical Ozone, 0 3 , is a reactive gas; in the upefit on mankind, right? problem since penicillin." In chemical per atmosphere, it blocks harmful soBENGT: Oxygen was good for people shorthand, it meant discovering how to in lar radiation. before it was "discovered!" troduce oxygen into the inaccessible C-ll And then Mme. Lavoisier's conclusion Appearance: Colorless, odorless gas at position ofring C of some readily available room temperature; pale blue as a liqof the play: "Imagine what it means to un plant sterol. And while a single issue in the uid and a solid; faintly blue with a derstand what gives a leaf its color! And 1951 Journal ofthe Amencan Chemical Soci how it turns red. What makes a fever fall, brackish odor as gaseous ozone. ety recorded the completion ofno less than Behavior: Oxygen supports combustion a flame burn. Imagine!" three such successful solutions, the earli and combines with most elements to est submission date bore the unlikely ad give both solid and gaseous oxides. Carl Djerassi isaplaywright, novelist, andprodress, "Syntex, S.A., LagunaMayran413"— fessor of chemistry emeritus at Stanford Universi Uses: Essential for respiration. Oxygen an industrial area of Mexico City across is used in steelmaking, in metal cutting, ty. He has won both the National1Medalfoj:Science from a tortilla stand—in marked contrast and in the chemicals industry to make (forthefirstsynthesisof asteroid'oral'contraceptive) to the fancy Rahway Ν J., and Cambridge, and the National Medal of Technology (forpro methanol and ethylene oxide. Mass., addresses of our competitors. moting new approaches to insect control).
O
46
C & E N / S E P T E M B E R 8, 2 0 0 3
HTTP://WWW.CEN-ONLINE.ORG
