Thread by @KRHornberger

🧵 I won’t wade too far into the debate du jour re: the Nobel and Hajos (who is alive), Parrish, Eder, Sauer, and Wiechert. But maybe a slight aside on the Hajos-Parrish ketone and its slightly larger cousin, the Wieland-Miescher ketone. 1/

The Hajos-Parrish and Wieland-Miescher ketones have had a big impact on steroid synthesis. They’re still central to teaching organic synthesis in the first year of grad school (AFAIK). 2/
en.wikipedia.org/wiki/Wieland%E…

It’s not clear to me that the asymmetric Hajos-Parrish and Wieland-Miescher ketone syntheses were, by themselves, enough to unlock the tumblers of the organocatalysis universe. Otherwise, why did it take another ~30 years to get around to it? 3/

Anyway, on to the point of the story. It’s 1998 and I’m taking the second semester of the graduate organic synthesis course at Columbia. Sam Danishefsky is teaching, filling the board with steroid total syntheses, one after another, entirely from memory. 4/

Danishefsky pauses midway, turns, and remarks: “If one is unfamiliar with the Wieland-Miescher ketone, one cannot be considered a player. Of course, even if one does know the Wieland-Miescher ketone, that doesn’t make one a player. But if you don’t, then you aren’t.” 5/

(That’s it. That’s the story.) /end