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Synthesizing complex and diverse terpenes from simple phenols

Nature prepares diverse terpene architectures in a three-step process starting from isoprene building blocks. A new three-step synthetic procedure is introduced to prepare terpenes starting from readily available phenols. Similarly to those used in nature, this pathway provides reliable and efficient access to diverse and complex terpene architectures.

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Fig. 1: Main design for diverse terpene synthesis.

References

  1. Christianson, D. W. Structural and chemical biology of terpenoid cyclases. Chem. Rev. 117, 11570–11648 (2017). This review article presents the chemical biology of terpenoid cyclases and their role in complex chemical reactions.

    Article  CAS  Google Scholar 

  2. Kanda, Y. et al. Two-phase synthesis of Taxol. J. Am. Chem. Soc. 142, 10526–10533 (2020). This paper reports the divergent synthesis of Taxol through cyclase/oxidase phases.

    Article  CAS  Google Scholar 

  3. Maruoka, K., Sato, J., Banno, H. & Yamamoto, H. Organoaluminum-promoted rearrangement of allyl phenyl ethers. Tetrahedron Lett. 31, 377–380 (1990). This paper reports the first use of bulky aluminium reagents for the selective dearomatization of prenyl phenol ethers.

    Article  CAS  Google Scholar 

  4. Nugent, W. A. & RajanBabu, T. V. Transition-metal-centered radicals in organic synthesis. Titanium(III)-induced cyclization of epoxy olefins. J. Am. Chem. Soc. 110, 8561–8562 (1988). This paper reports titanium(iii)-promoted ring openings of epoxides and the subsequent radical cyclization of epoxy olefins.

    Article  CAS  Google Scholar 

  5. Yao, C., Dahmen, T., Gansäuer, A. & Norton, J. Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis. Science 364, 764–767 (2019). This paper reports the ring opening of epoxides through cooperative catalysis.

    Article  CAS  Google Scholar 

Download references

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This is a summary of: Salahi, F. et al. The synthesis of diverse terpene architectures from phenols. Nat. Synth. https://doi.org/10.1038/s44160-022-00051-2 (2022).

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Synthesizing complex and diverse terpenes from simple phenols. Nat. Synth 1, 271–272 (2022). https://doi.org/10.1038/s44160-022-00047-y

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