183293-41-6

Upstream product

• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 98-59-9 p-toluenesulfonyl chloride 
• 84341-89-9 (2S)-(+)-2-methyl-3-(toluene-4-sulfonyloxy)propionic acid methyl ester 

Downstream Products

• 183293-42-7 Toluene-4-sulfonic acid (2S,3S,4R)-5-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester 
• 868547-99-3 (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene 
• 944154-87-4 (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methylhex-5-enyl 4-methylbenzenesulfonate 
• 1361551-13-4 (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-methyl-7-(tosyloxy)heptanoic acid 
• 1436866-91-9 C₂₁H₃₄O₆SSi 
• 501015-40-3 (2S,3S)-(+)-toluene-4-sulfonic acid 3-hydroxy-2-methylhex-5-enyl ester 
• 874914-31-5 (2S,3R)-3-hydroxy-2-methylhex-5-enyl 4-methylbenzenesulfonate 
• 1137669-56-7 C₁₆H₂₄O₄S 
• 1137669-57-8 C₁₆H₂₄O₄S 
• 183293-44-9 Propionic acid (1R,2S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-[(S)-1-methyl-2-(toluene-4-sulfonyloxy)-ethyl]-propyl ester 
• 183293-43-8 Toluene-4-sulfonic acid (2S,3R,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentyl ester 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 868548-00-9 toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester 

Relevant academic research and scientific papers

Modular total syntheses of mycolactone A/B and its [2H]-isotopologue

A modular total synthesis of mycolactone A/B, the exotoxin produced by Mycobacterium ulcerans, has been achieved through the orchestration of several Pd-catalyzed key steps. While this route leads to a mixture of the natural product and its C12 epimer (4:

Synthesis of C14-C21 acid fragments of cytochalasin Z8: Via anti -selective aldol condensation and B -alkyl Suzuki-Miyaura cross-coupling

An efficient synthesis of the C14-C21 acid fragment of cytochalasin Z8 was accomplished in 10 steps with 14% overall yield. Boron-mediated anti-selective aldol condensation and Pd(OAc)2-Aphos-Y-catalysed B-alkyl Suzuki-Miyaura cross-

STRUCTURAL VARIANTS OF MYCOLACTONES FOR USE IN MODULATING INFLAMMATION, IMMUNITY AND PAIN

The present invention is related to variants of mycolactones of formula (I), processes for the preparation thereof, pharmaceutical compositions thereof and their use in modulating inflammation, immunity and pain. Y-O-W (I), wherein Y and W are as defined in claim 1.

Structural variants of mycolactones for use in modulating inflammation, immunity and pain

The present invention is related to variants of mycolactones of formula (I), processes for the preparation thereof, pharmaceutical compositions thereof and their use in modulating inflammation, immunity and pain. ???????? Y-O-W?????(I) wherein Y and W are as defined in claim 1.

A diverted total synthesis of mycolactone analogues: An insight into buruli ulcer toxins

Mycolactones are complex macrolides responsible for a severe necrotizing skin disease called Buruli ulcer. Deciphering their functional interactions is of fundamental importance for the understanding, and ultimately, the control of this devastating mycobacterial infection. We report herein a diverted total synthesis approach of mycolactones analogues and provide the first insights into their structure-activity relationship based on cytopathic assays on L929 fibroblasts. The lowest concentration inducing a cytopathic effect was determined for selected analogues, allowing a clear picture to emerge by comparison with the natural toxins.

Asymmetric total synthesis of the immunosuppressant (-)-pironetin

(Chemical Equation Presented) A short, enantioselective total synthesis of the title compound 1 is described. The 14-step synthesis features a highly stereoselective Brown-type pentenylation and a onepot hydrosilylation/ring- closing metathesis (RCM)/prot

Domino intramolecular enyne metathesis/cross metathesis approach to the xanthanolides. Enantioselective synthesis of (+)-8-epi-xanthatin

The first total synthesis of (+)-8-epi-xanthatin (1) has been achieved in 14 steps starting from the commercially available ester 24, which was converted into aldehyde 23 in six steps. An enantioselective aldol reaction of 23 gave 30, which was transformed into triflate 22 in four steps, setting the stage for a palladium-catalyzed carbonylation reaction to form acrylate 34. Compound 34 was then subjected to a deprotection/lactonization sequence to furnish enyne 21, which underwent a domino enyne ring-closing metathesis/cross metathesis process to form a seven-membered carbocycle and (E)-conjugated dienone, thereby completing the synthesis of 1. This domino ruthenium-catalyzed metathesis reaction thus serves as an efficient method to construct the core of xanthanolide and other sesquiterpene lactones.

Application of a domino intramolecular enyne metathesis/cross metathesis reaction to the total synthesis of (+)-8-epi-xanthatin

(Chemical Equation Presented) The first total synthesis of the novel sesquiterpene lactone (+)-8-epi-xanthatin (1) has been achieved starting from the commercially available ester 8. The synthesis features an asymmetric aldol reaction and palladium-catalyzed carbonylation/lactonization sequence leading to 4 and a domino ring-closing enyne metathesis/cross metathesis reaction to afford 1.

Total Syntheses of Amphidinolide T1, T3, T4, and T5

A concise, flexible, and high yielding entry into the family of amphidinolide T macrolides, a series of cytotoxic natural products of marine origin, has been developed. All individual members, except amphidinolide T3 (3), derive from compound 39 as a comm

Total synthesis of amphidinolide T4

Organometallic chemistry in general and catalysis in particular are used in the first total synthesis of amphidinolide T4 (see scheme); a prototype member of a series of macrolide antibiotics of marine origin with rings containing an odd number of carbon