155897-72-6Relevant articles and documents
Enantiomerically Pure Pyrrolidine Derivatives from trans-4-Hydroxy-L-proline By Electrochemical Oxidative Decarboxylation and Titanium-Tetrachloride-Mediated reaction with Nucleophiles
Renaud, Philippe,Seebach, Dieter
, p. 1704 - 1710 (1986)
Preparative electrolysis of N-methoxycarbonyl-O-hydroxyproline 4 in MeOH leads to substitution of the COOH by a MeO group (oxidative decarboxylation).The mixture 5 of the two diastereoisomers (ca. 1:1) thus obtained was reacted in CH2Cl2 with nucleophilic silylated compounds (such as allylsilane, silyl cyanide and 1-phenyl-1-silyloxyethane) or with trimethyl phosphite in the presence of TiCl4 to give 2-allyl-, 2-cyano-, 2-(2-oxo-2-phenylethyl)- and 2-phosphono-substituted hydroxypyrrolidines, respectively, with high diastereoselectivities (>= 90 percent, products 6-12).The configuration of two of the products (6/7 and 8/9) was shown to be cis.
Ring enlargement by alkylated 3-hydroxybutyrates: A synthesis of (12S, 13R)-(-)-12-methyl-13-tetradecanolide
Kraft,Tochtermann
, p. 10875 - 10882 (1995)
TBS-protected iodo alcohols 6 were prepared via Frater alkylation and applied in the synthesis of optically active macrolides 5 and 10. By ring enlargement of cyclodecanone (7) the superposition molecule 5 of two macrocyclic odorants was synthesized and a conformationally fixed tricyclic macrolide 11 constructed.
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 and Configurational Assignment of AscospiroketalA
Chang, Stanley,Hur, Soo,Britton, Robert
supporting information, p. 16646 - 16653 (2015/11/09)
The total synthesis of the marine fungus-derived natural product ascospiroketal is described. This concise synthesis relies on a unique AgI-promoted tandem cascade cyclization that provides direct access to the correctly configured tricyclic core of the natural product from a linear precursor. The synthesis of candidate stereostructures of ascospiroketalA allowed for the confident assignment of both the relative and absolute stereochemistry of this unusual octaketide.
Discovery of a potent, metabolically stabilized resorcylic lactone as an anti-inflammatory lead
Du,Matsushima,Spyvee,Goto,Shirota,Gusovsky,Chiba,Kotake,Yoneda,Eguchi,DiPietro,Harmange,Gilbert,Li,Davis,Jiang,Zhang,Pelletier,Wong,Sakurai,Yang,Ito-Igarashi,Kimura,Kuboi,Mizui,Tanaka,Ikemori-Kawada,Kawakami,Inoue,Kawai,Kishi,Wang
supporting information; scheme or table, p. 6196 - 6199 (2010/06/19)
With bioactivity-guided phenotype screenings, a potent anti-inflammatory compound f152A1 has been isolated, characterized and identified as the known natural product LL-Z1640-2. Metabolic instability precluded its use for the study on animal disease model
