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DOI: 10.1055/s-0041-1738000
The First Total Synthesis of (±)-Forskolin
Total Synthesis of (±)-Forskolin.
J. Am. Chem. Soc. 1988;
110: 3672-3673
DOI: 10.1021/ja00219a059

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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