What was the first demonstration of organic total synthesis?

1 Answer
Ernest Z.
Jan 16, 2016

The first total synthesis was the Finnish chemist Gustav Komppa's total synthesis of camphor.

Explanation:

In 1903, Komppa succeeded in synthesizing camphoric acid from diethyl oxalate and diethyl β,β-dimethylglutarate.

A few years earlier, Haller and Blanc had converted camphoric acid to camphor, so this constituted a total synthesis of camphor.

At the time, camphor was a scarce natural product with a worldwide demand.

Komppa realized this and began industrial production of camphor in 1907.

For the terminally curious, here's a summary of the steps.

#underbrace(("COOCH"_2"CH"_3)_2)_color(red)("diethyl oxalate") + underbrace(("CH"_3)_2"C"("CH"_2"COOCH"_2"CH"_3)_2)_color(red)("diethyl β,β-dimethylglutarate") stackrelcolor(blue)("NaOEt"color(white)(X))(→)#

I
diethyl diketocamphorate (I)

#"CH"_3"I/Na" →#

II

#"Zn/HCl →"#

III

#"HI/red P" →#

IV

#"HBr" →#

β-bromocamphoric acid V

#"Zn/HCl" →#

Camphoric acid VI

#"Acetic anhydride, Δ" →#

Camphoric Anhydride VII

#"Na(Hg)" →#

α-Campholide VIII

#"KCN"#

IX

#"OH"^("-")("aq"), Δ →#

Homocamphoric acid X

#"Ca salt", Δ →#

Camphor XI

Related questions
See all questions in Brief History of Organic Chemistry
Impact of this question
3601 views around the world
You can reuse this answer
Creative Commons License