The Half Decent Pharmaceutical Chemistry Blog

Tonight, we disappoint James Watson as we try to make the gayest synthesis ever!

Hello and welcome! In the past, homosexuals were stereotyped as shy, well-mannered, polished but always repressed and frustrated little men, who, surrounded by intolerant idiots, believed there was somehow something wrong with them and they had a sort of terrible dysfunction that must be kept secret. These day, fortunately, people are free to live their sexuality as they prefer in pretty much all the developed world. I mean, there’re still disgusting people who firmly believe homosexuality to be a disease, especially in the Vatican and the USA (not to mention all those places where women are considered to belong to an inferior species), but, since so many people come out nowadays and a little bit of common sense seems to be spreading around the world, homosexuals don’t fell that lonely any more. This progressive change has been typified by a radically different, stereotyped image of the homosexual guy, who is now a bronzed, sculptured, muscle-man, who spends most of his day in gyms, perhaps a bit too obsessed with his physical appearance and usually dressed better (and, according to many women, better-looking as well) than his straight counterpart (who may become a metro-sexual: a straight man who has taken up many homosexuals’ habits because he has realised they are incredibly helpful to pull women).
To sum up, gays have become the modern, testosteronic machos.

So, to synthesize testosterone, the music can only be “Macho Man” by Village People, as this is an impossibly (and undoubtedly) gay synthesis. Can’t you imagine Village People dressed like chemists, performing the synthesis for a new edition of the video? It features two name reactions, named after two chemists who, I guess, should become gay-icons for all gay chemists out there: Ernst Otto Beckmann and Rupert Viktor Oppenauer.

What to say about the pharmacology of testosterone? Well, normally this hormone is produced by our body where, converted to dihydrotestosterone by a reductase, regulates the expression of a number of genes, ultimately triggering the development of secondary sex characteristics in men through growth-promoting properties, which aren’t limited to reproductive organs, but affect also  bones (testosterone causes epiphysial closure, for example).
Still, sometimes some more testosterone has to be administered: pituitary deficiencies, gynaecologic disorders, breast tumours in pre-menopausal women, recovery from debilitating diseases, some kinds of anaemias or a delayed puberty, all require an extra testosterone.
There are, moreover, those musclemen who self-administer testosterone to increase their muscles. Funnily, these idiots expose themselves to worrying adverse effects such as gynecomastia and azoospermia.

The synthesis begins with a protection of the hydroxyl and the synthesis of an oxime, which serves as substrate for the following Beckmann rearrangement.
Briefly, Beckmann rearrangement is a very elegant reaction with employs only sulphuric acid to catalyse the conversion of an oxime into an amide. Once you’ve yield the amide, though, it immediately undergoes acid hydrolysis.
The yielded carbonyl is then reduced, with hydrogen and Raney nickel, and protected using benzoyl chloride.
Finally, the 3-OH is deprotected, so that it could undergo a lovely Oppenauer oxidation, with aluminium tert-butoxide and acetone. The synthesis finishes with the deprotection of the other hydroxyl.
Yes, I must admit that, being an old-fashioned, straight lad, I couldn’t resist and used the picture of the beautiful ladies above for the last step. This, however, doesn’t change the fact that this remains a very, gay synthesis.

Good night and enjoy yourself!