468756-88-9Relevant academic research and scientific papers
In vitro kinetic study of the squalestatin tetraketide synthase dehydratase reveals the stereochemical course of a fungal highly reducing polyketide synthase
Liddle, Emma,Scott, Alan,Han, Li-Chen,Ivison, David,Simpson, Thomas J.,Willis, Christine L.,Cox, Russell J.
supporting information, p. 1727 - 1730 (2017/02/10)
Six potential diketide substrates for the squalestatin tetraketide synthase (SQTKS) dehydratase (DH) domain were synthesised as N-acetyl cysteamine thiolesters (SNAC) and tested in kinetic assays as substrates with an isolated DH domain. 3R-3-hydroxybutyryl SNAC 3R-16 was turned over by the enzyme, but its enantiomer was not. Of the four 2-methyl substrates only 2R,3R-2-methyl-3-hydroxybutyryl SNAC 2R,3R-8 was a substrate. Combined with stereochemical information from the isolated SQTKS enoyl reductase (ER) domain, our results provide a near complete stereochemical description of the first cycle of beta-modification reactions of a fungal highly reducing polyketide synthase (HR-PKS). The results emphasise the close relationship between fungal HR-PKS and vertebrate fatty acid synthases (vFAS).
Total synthesis of bafilomycin A1
Kleinbeck, Florian,Fettes, Gabriela J.,Fader, Lee D.,Carreira, Erick M.
supporting information; experimental part, p. 3598 - 3610 (2012/05/04)
A convergent synthesis of bafilomycin A1, a potent inhibitor of V-type ATPases, is presented. The synthesis relies on the zinc triflate mediated diastereoselective addition of a complex enyne to a sensitive aldehyde as the key fragment coupling. A ruthenium-catalyzed trans-reduction of the resulting propargylic enyne efficiently installs the required C10-C13 trans,trans-diene subunit, implementing an alternative strategy to traditional palladium-catalyzed cross-coupling strategies. A highly selective oxidation of a secondary hydroxyl group in a triol sets the stage for the completion of the synthesis. Copyright
New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies
Neri, Claudia,Williams, Jonathan M. J.
, p. 835 - 848 (2007/10/03)
This paper describes how enantiomerically enriched Evans auxiliaries can be successfully prepared by either an enzymatic desymmetrisation strategy or an asymmetric synthesis using racemic auxiliaries and an enzymatic resolution. Desymmetrisation of N-Boc-protected serinol has been achieved in good yield and high enantiomeric excess using porcine pancreas lipase. This has been exploited in different ways to prepare enantiomerically enriched (4R)- and (4S)-substituted 2-oxazolidinones. In another approach to asymmetric synthesis, starting from a racemic Evans auxiliary, by means of a diastereoselective aldol reaction coupled with a lipase-catalysed resolution, we achieved the preparation of enantiomerically enriched β-hydroxy acids and enantiomerically enriched 2-oxazolidinones.
Racemic auxiliaries: Applications to asymmetric synthesis
Neri, Claudia,Williams, Jonathan M.J.
, p. 4257 - 4260 (2007/10/03)
Racemic auxiliaries have been successfully used to achieve asymmetric synthesis. Racemic Evans aldol products were obtained from racemic acyl oxazolidinones with good diastereocontrol. The enantiomers of the racemic aldol products were resolved by a lipase-catalysed acylation reaction. Hydrolysis afforded enantiomerically enriched oxazolidinones and enantiomerically enriched β-hydroxy acids.
