Application of Pauson-Khand Reaction in the Total Synthesis of Terpenes

Summary

This research reviews an important chemical reaction called the Pauson-Khand reaction and its use in synthesizing natural compounds called terpenes. These compounds are found in plants and have various medicinal properties. The reaction helps chemists build complex molecules more efficiently than traditional methods. Impacts on everyday life: – Enables more efficient production of medicines derived from natural sources – Helps develop new drug candidates for treating cancer, HIV, and inflammatory diseases – Reduces the cost and environmental impact of producing therapeutic compounds – Advances our understanding of how to make complex molecules found in nature – Could lead to new treatments for various diseases through improved synthetic methods

Background

The Pauson-Khand reaction (PKR) is a formal [2 + 2 + 1] cycloaddition involving an alkyne, an alkene and carbon monoxide mediated by a hexacarbonyldicobaltalkyne complex to yield cyclopentenones in a single step. This versatile reaction has become a method of choice for the synthesis of cyclopentenone and its derivatives since its discovery in the early seventies.

Objective

This review aims to highlight and analyze the applications of the Pauson-Khand reaction in the total synthesis of various terpene natural products, including monoterpenes, diterpenes, sesquiterpenes and their derivatives.

Results

The review demonstrates that the Pauson-Khand reaction has been successfully applied in the total synthesis of many complex terpene natural products. Key examples include the synthesis of Japanese hop ether, mintlactone, iridoids, hamigeran B, ingenol, cyanthiwigins, ryanodol, and various other mono-, di- and sesquiterpenes. The reaction allows efficient construction of cyclopentenone rings and complex polycyclic frameworks.

Conclusion

The Pauson-Khand reaction proves to be a powerful and versatile synthetic tool for constructing complex terpene frameworks. Its ability to form multiple bonds and rings in a single step, along with good stereoselectivity, makes it particularly valuable in natural product synthesis. Recent developments in catalytic and asymmetric variants have further expanded its utility.
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