99328-37-7

Upstream product

• 66767-60-0 methyl (2S,3S)-3-hydroxy-2-methylbutanoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 34293-67-9 methyl (2R,3S)-3-hydroxy-2-methylbutanoate 
• 2689-68-1 methyl 4-oxotetrahydrothiophene-3-carboxylate 
• 53562-86-0 (S)-3-hydroxybutyric acid methyl ester 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 84230-99-9 methyl (3R,4R)-4-hydroxytetrahydrothiophene-3-carboxylate 

Relevant academic research and scientific papers

Total synthesis of ascospiroketal a through a agI-promoted cyclization cascade

The total synthesis of four candidate stereostructures for the marine octaketide ascospiroketal A have been achieved. These concise and highly stereocontrolled syntheses feature a unique AgI-promoted cyclization cascade involving an oxetanyl ketochlorohydrin to access the entire tricyclic core of the natural product in one step. These syntheses also establish the full stereochemistry for the ascospiroketal natural products.

In vitro kinetic study of the squalestatin tetraketide synthase dehydratase reveals the stereochemical course of a fungal highly reducing polyketide synthase

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

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.

The prins reaction using ketones: Rationalization and application toward the synthesis of the portentol skeleton

We report a TMSI-promoted Prins cyclization reaction with ketones as carbonyl partners to prepare polysubstituted chiral spirotetrahydropyrans. In the presence of racemic 2-methylcyclohexanone a dynamic kinetic resolution occurred affording one stereoisom

Discovery of a potent, metabolically stabilized resorcylic lactone as an anti-inflammatory lead

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

MACROCYCLIC COMPOUNDS USEFUL AS PHARMACEUTICALS

The present invention provides compounds having formula (I), and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of various disorders including inflammatory or autoimmune disorders, and disorders involving malignancy or increased angiogenesis, wherein R1 -R11, t, X, Y, Z, and n are as defined herein.

The Sense of Asymmetric Induction on Addition to α-Chiral Aldehydes

On addition of (E)-crotylboronates to aldehydes with an α-methyl branch the expected Cram-products are formed predominantly.On addition of the (Z)-crotylboronates to the same aldehydes the anti-Cram-products are formed in preference.Hence, the sense of 1,2-asymmetric induction depends also on the nature of the achiral reagent.The reasons for and the conditions leading to such a phenomenon are discussed.