Total Synthesis of the Natural Herbicide MBH‐001 and Analogues

The first total synthesis of the natural herbicide MBH‐001 (1) is reported. Structurally it is a 2‐methyloxazol‐5 (2H)‐one with a (1‐hydroxyethyl) substituent at the 2‐position. By relying on cyclic nitrones, a flexible route to MBH‐001 and relevant analogues was developed. Key steps include the reaction of a 2‐hydroxyimino ester with an aldehyde to form a 5‐oxo‐2,5‐dihydrooxazole 3‐oxide. In an aldol‐type reaction, the anion of these cyclic nitrones reacted with an aldehyde at the 2‐position. A final reduction of the nitrone to the corresponding imine using zinc led to the target compounds. The cyclic nitrones are also accessible by reacting an α‐keto acid with an oxime. These two versatile synthetic routes enabled us to prepare the first MBH‐001 analogues for structure activity relationship analysis of the herbicidal efficacy. Thus, furthering our aim of developing new herbicides to tackle the ever‐growing problem of weed resistance.

Angaben zum Objekt

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Total Synthesis of the Natural Herbicide MBH‐001 and Analogues ; volume:2020 ; number:15 ; year:2020 ; pages:2271-2290 ; extent:20 ; European journal of organic chemistry ; 2020, Heft 15 (2020), 2271-2290 (gesamt 20)

Beteiligte, Orts- und Zeitangaben

• Urheber: Kuhn, Birgit ; Barber, David M. ; Dietrich, Hansjörg ; Döller, Uwe ; Hoffmann, Michael G. ; Schmutzler, Dirk ; Schnatterer, Stefan ; Maier, Martin E. ; Kocakaya, Tamer ; Morkunas, Marius

Weitere Informationen

• DOI: 10.1002/ejoc.202000294
• URN: urn:nbn:de:101:1-2022062411290862308608
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Letzte Aktualisierung: 15.08.2025, 07:31 MESZ