Total Synthesis 12: Cephanolide A

Cephanolide A is a natural product that belongs to a family of diterpenoids that have shown a broad range of bioactivity, including antiviral and antitumor properties as well as cytotoxic activity against human cancer cell lines.

Synthesis steps:
1. Triflation of commercially available hydroxymethylindanone.
2. Suzuki cross-coupling.    • Suzuki Coupling  
3. Suzuki cross-coupling.
4. Cascade silyl enol formation and intramolecular Diels–Alder cycloaddition.    • Diels-Alder Reaction  
5. Modified Mukaiyama hydration.
6. Olefination.
7. Riley oxidation.    • Riley Oxidation  
8. Hydrogenation and epimerization of the methyl-bearing stereocentre.
9. Reduction of the ketone group.
10. Suarez oxidation conditions for the formation of the THF ring.
11. Classical Barton–McCombie deoxygenation.    • Barton-McCombie Reaction  
12. Oxygenation of the benzene ring using cyclopropane malonyl perodixe.

Reference:
J. Am. Chem. Soc. 2021, 143, 2710. https://doi.org/10.1021/jacs.1c00293

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