Wieland–Miescher ketone

About: Wieland–Miescher ketone is a research topic. Over the lifetime, 88 publications have been published within this topic receiving 938 citations. The topic is also known as: 8a-Methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione.

Regio- and stereoselective functionalizations of the Wieland-Miescher ketone derivatives at the C-8 position

Abstract: New efficient methods for stereoselective hydroxymethylation, hydroxylation, and thiophenylation at the C-8 position of the Wieland-Miescher ketone derivatives (2__--4__-) have been developed by diverse modifications from the Kirk-Petrow reaction, which involve autoxidation for the hydroxylation.

Mechanistic Study on the Asymmetric Synthesis of the Wieland-Miescher Ketone and Analogs

Abstract: The organocatalyzed synthesis of the Wieland‐Miescher ketone (WMK) via N‐sulfonyl‐binamprolinamide catalysis was investigated using experimental and computational tools. A mechanistic proposal is presented describing the origin of the high enantioselectivity, which rivals that of aldolases. The computational study reveals that the role of the prolinamide catalyst is to lower the reaction barrier and determine the stereoselectivity of the product achieved, while the role of the carboxylic acid is to facilitate proton transfer steps. The effect of the acid co‐catalyst was confirmed by experiments. The role of the structure of the BINAM backbone and the effect of the sulfonamide group are uncovered experimentally and computationally. Calculations show that a rigid highly defined catalytic pocket due to covalent and steric interactions induces conformational changes in the triketone substrate to maximize interactions.

Enantioselective synthesis of a taxol C ring

Abstract: An enantioselective synthesis of a C ring of taxol has been accomplished. The key step is an oxidative cleavage of a derivative of the Wieland-Miescher ketone. A first attempt of a Shapiro reaction modelling the coupling of the C ring with the A fragment of taxol was also successful. © 2011 Institute of Organic Chemistry and Biochemistry.

(Sa,S)‐N‐[2′‐(4‐Methylphenylsulfonamido)‐1,1′‐Binaphthyl‐2‐Yl]Pyrrolidine‐2‐Carboxamide: An Organocatalyst for the Direct Aldol Reaction

Abstract: (Sa)-(-)-1,1′-Binaphthyl-2,2′-diamine p-Toluenesulfonyl chloride Pyridine N-(tert-Butoxycarbonyl)-L-proline Ethyl chloroformate Triethylamine Trifluoroacetic acid Keywords: (Sa,S)-N-[2′-(4-Methylphenylsulfonamido)-1,1′-binaphthyl-2′-yl]-pyrrolidine-2-carboxamide; direct asymmetric aldol reactions; BINAM-prolinamides; Wieland Miescher ketone (WMK); (Ra,R)-N-[2′-(4-methylphenylsulfonamido)-1,1′-binaphthyl-2-yl]pyrrolidine-2-carboxamide; hydrogen bonding

Access to Enantiomerically Pure Intermediates for (−)-Geosmin Synthesis Starting from (4aS,5S)-4,4a,5,6,7,8-Hexahydro-5-hydroxy-4a-methyl-naphthalen-2(3H)-one

Abstract: Enantiomerically pure key intermediates for the synthesis of the natural enantiomer of geosmin were synthesized from (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one.