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

Sakai, Naomi; Sorde, Nathalie; Matile, Stefan

doi:10.3390/61100845

Scientific article

English

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

ContributorsSakai, Naomi

; Sorde, Nathalie; Matile, Stefan

Published inMolecules, vol. 6, no. 11, p. 845-851

Publication date2001

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

Keywords

Bioorganic chemistry
Claisen condensation
Enzyme mimics
Polyketide synthesis

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

SAKAI, Naomi, SORDE, Nathalie, MATILE, Stefan. Mg2+-Imidazol-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis? In: Molecules, 2001, vol. 6, n° 11, p. 845–851. doi: 10.3390/61100845

Article

Identifiers

PID : unige:7929
DOI : 10.3390/61100845

494views

0downloads

Creation21/06/2010 10:28:41

First validation21/06/2010 10:28:41

Update14/10/2025 06:56:08

Status update14/03/2023 15:47:20

Last indexation16/02/2026 06:56:21

Archive ouverte UNIGE

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

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

Technical informations