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Synfacts 2024; 20(04): 0425
DOI: 10.1055/s-0043-1773212
Innovative Drug Discovery and Development

The First Total Synthesis of Camphor and the Industrial Standard

Contributor(s):
Dirk Trauner
,
Robert Gaston Jr.
Komppa G. University of Helsinki, Finland
Die vollständige Synthese der Camphersäure und Dehydrocamphersäure.

Ber. Dtsch. Chem. Ges. 1903;
36: 4332-4335
DOI: 10.1002/cber.190303604115
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Key words

camphor - Wagner–Meerwein rearrangement - non-classical carbocation

Significance

Camphor is a common terpene building block in natural product synthesis. Notably, the synthesis of Taxol by the Holton group commences with camphor. Komppa’s pioneering synthesis set the standard for the future industrial route starting from α-pinene and taking advantage of sequential Wagner–Meerwein rearrangements and non-classical cations to enable rapid access to camphor.


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Comment

Komppa’s camphor synthesis begins with a double Claisen condensation, a diol reduction, and a red phosphorous-mediated elimination. From there, camphoric acid and campholide are prepared which lead to an interesting Ca(OH)2-promoted decarboxylative Dieckmann condensation, presumably through a calcium chelate.


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Publication History

Article published online:
13 March 2024

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