Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?

doi:10.3390/61100845

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Molecules 2001, 6(11), 845-851; doi:10.3390/61100845

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Mg²⁺-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?

Naomi Sakai, Nathalie Sordé and Stefan Matile*

Department of Organic Chemistry, University of Geneva, CH-1211 Geneva 4, Switzerland

* Author to whom correspondence should be addressed.

Received: 3 September 2001; in revised form: 15 October 2001 / Accepted: 16 October 2001 / Published: 31 October 2001

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Abstract: We report that a subtle balance of carbanion reactivity, leaving group activation, and pKa of the catalyst is required for efficient self-condensation of thiomalonates to thioacetoacetates in up to 71% yield under “biomimetic” conditions originally proposed by Kobuke and Yoshida (Tetrahedron Lett. 1978, 19, 367).

Keywords: Bioorganic chemistry; Claisen condensation; enzyme mimics; polyketide synthesis

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MDPI and ACS Style

Sakai, N.; Sordé, N.; Matile, S. Mg²⁺-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis? Molecules 2001, 6, 845-851.

AMA Style

Sakai N, Sordé N, Matile S. Mg²⁺-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis? Molecules. 2001; 6(11):845-851.

Chicago/Turabian Style

Sakai, Naomi; Sordé, Nathalie; Matile, Stefan. 2001. "Mg²⁺-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?" Molecules 6, no. 11: 845-851.

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