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Synfacts 2022; 18(05): 0563
DOI: 10.1055/s-0041-1738000
Chemistry in Medicine and Biology

The First Total Synthesis of (±)-Forskolin

Contributor(s):
Dirk Trauner
,
Tongil Ko
Corey EJ, *, da Silva Jardine P, Rohloff JC. Harvard University, Cambridge, USA
Total Synthesis of (±)-Forskolin.

J. Am. Chem. Soc. 1988;
110: 3672-3673
DOI: 10.1021/ja00219a059.
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Key words

Forskolin - cAMP - Grieco elimination - hetero-Diels–Alder reaction

Significance

Forskolin is a diterpenoid isolated from Coleus barbatus that raises cyclic AMP (cAMP) levels by activating the adenyl cyclase enzyme, which, in turn, converts ATP into cAMP. cAMP is an important second messenger molecule for signal transduction and forskolin is a vital tool to investigate the role of cAMP in various cellular processes. In 1988, Corey and co-workers reported the first total synthesis of forskolin.


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Comment

The opening step of the total synthesis was a Diels–Alder reaction of hydroxy diene A with acetylenic acid B. The key step of the synthesis is the photocyclization of C followed by a singlet oxygen Diels–Alder reaction leading to D. This elegant transformation allowed for the stereoselective formation of the C-ring of forskolin and for the introduction of the C1 hydroxy group in the correct geometry.


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Publication History

Article published online:
20 April 2022

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