Avoid Protecting Groups

Author:

Abstract

Protecting groups have become standard in organic synthesis, yet they contribute to synthetic inefficiency, adding two extra steps for each protecting group—putting it on and taking it off. Protecting groups can be categorized in several ways. Here, we have grouped them according to the conditions used to remove them: acid, base, fluoride, Pd, hydrogenation, or oxidation labile. Different functional groups have different reactivities that must be considered in designing a synthesis. Protic acids, α-carbon acids, electrophiles, and bases/nucleophiles each require different consideration. In the synthesis of Simvastatin, Codexis created a highly specific LovD evolved enzyme to acylate one of three 2° hydroxyls of Lovastatin. This avoided the protection and deprotection steps required in the two other commercial syntheses of Simvastatin. Baran described eight concepts to guide the design of protecting-group-free synthesis of complex natural products: convergence, maximize C–C bond formation, minimize redox reactions, linearly change oxidation state, cascade reactions, exploit innate reactivity, invent new reactions, and biomimetic synthesis. Baran incorporated these concepts into an efficient 10-step synthesis of the complex natural product Ambiguine H without any protecting groups. Krische orchestrated a highly efficient, convergent synthesis of Swinholide A with only two protecting groups.

Publisher

The Royal Society of Chemistry

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