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A 15-step synthesis of (+)-ryanodol
Kangway V Chuang1, Chen Xu1, Sarah E Reisman2
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Science (New York, N.Y.)
|August 27, 2016
Summary
(+)-Ryanodol, a complex diterpenoid, was synthesized in 15 steps. This efficient method for synthesizing ryanodine receptor modulators utilizes key reactions for rapid carbon framework construction and oxygen installation.
Area of Science:
- Organic Chemistry
- Molecular Biology
- Biophysics
Background:
- (+)-Ryanodine and (+)-ryanodol are complex diterpenoids that regulate intracellular calcium-ion release via ryanodine receptors.
- Ryanodine receptors are crucial for muscle excitation-contraction coupling and synaptic transmission.
- Structural modifications of these diterpenoids can impact their binding affinity and selectivity for ryanodine receptor isoforms.
Purpose of the Study:
- To develop a concise and efficient chemical synthesis for (+)-ryanodol.
- To explore strategic C-O bond constructions for streamlining polyhydroxylated terpene synthesis.
Main Methods:
- A 15-step synthesis of (+)-ryanodol from (S)-pulegone.
- Utilized a Pauson-Khand reaction for rapid carbon framework assembly.
- Employed SeO2-mediated oxidation for simultaneous installation of three oxygen atoms.
Main Results:
- Successfully synthesized (+)-ryanodol in a significantly reduced number of steps.
- Demonstrated the efficiency of the Pauson-Khand reaction and SeO2-mediated oxidation in this synthesis.
- Highlighted the importance of strategic C-O bond formations.
Conclusions:
- A short and efficient synthesis of (+)-ryanodol has been achieved.
- This synthetic route minimizes the need for protecting groups and redox adjustments.
- The strategy is applicable to the synthesis of other polyhydroxylated terpenes.
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