74183-94-1

Upstream product

• 65371-27-9 2-decen-9-olide (Z isomer) 
• 67400-99-1 (+/-)-phoracantholide J 
• 73842-98-5 2-benzenesulfonyl-9-hydroxydecanoate lactone 
• 4017-57-6 2-oxocyclononanecarboxylic acid ethyl ester 
• 1373273-37-0 (S)-5-hydroxyhexanal 
• 88980-13-6 (S)-hept-6-en-2-ol 
• 74791-43-8 (-)-(R)-4-oxodecan-9-olide 
• 35433-73-9 (R)-9-hydroxydecanoic acid 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 24395-10-6 (R)-hept-6-en-2-ol 
• 143956-84-7 (R)-5-hydroxyhexanal 
• 85881-64-7 (Z)-(R)-9-Hydroxy-dec-4-enethioic acid S-pyridin-2-yl ester 
• 85852-47-7 methyl (R)-9-hydroxy-4-decynoate 
• 85881-62-5 methyl (R)-9-hydroxy-4(Z)-decenoate 

Downstream Products

• 131111-68-7 (3S,9S)-3-methyl-9-hydroxy-decyl tosylate 
• 131111-71-2 (3R,9S)-3-methyl-9-hydroxy-decyl tosylate 
• 97466-68-7 (+/-)-pyrenolide B 

Relevant academic research and scientific papers

Stereoselective synthesis of (R)-(?) and (S)-(+)-phoracantholide I from (R)-(+)-γ-valerolactone

A concise total synthesis of (R)-(?)-phoracantholide I 1 and (S)-(+)-phoracantholide I 2 has been developed from (R)-(+)-γ-valerolactone 6. The key steps in the synthesis of these macrolides involved enzymatic reduction of Levulinic ester 4 by asymmetric dehydrogenase, Z-selective Wittig reaction of (4-carboxybutyl)triphenylphosphonium ylide 11 with lactol 7, and cyclization of seco-acid 8 using either a Yamaguchi lactonization protocol or a Mitsunobu protocol to afford (R)-(?)-phoracantholide I and (S)-(+)-phoracantholide I respectively.

Removable Silyl Group as a "masked Proton" in Oxy-2-oxonia(azonia)-Cope Rearrangement: Applications in Stereoselective Total Synthesis of Natural Macrolides

In the presence of a Lewis acid, trimethylsilyl-substituted β,γ-unsaturated ketones and aldehydes (imines) undergo nucleophilic addition to produce zwitterionic intermediates, followed by oxy-2-oxonia(azonia)-Cope rearrangements to give homoallylic esters (amides). In the case of TMS-containing 2-vinylcycloalkanones, the process results in ring-enlargement, providing 10- to 16-membered lactones. This protocol was applied to the total synthesis of (R)-phoracantholide I.

Silver carboxylate promoted lactonization: A general method applicable to prepare medium and large-sized lactones without high dilution or slow addition

Efficient and applicable approach to macrolactonizations, with ready availability of starting materials and simple operation, remains a challenging task for the organic community. We developed a 'freshman-can-do' protocol to medium- and large-sized lactones, not depending on high-dilution or slow addition techniques. Application of this method for the synthesis of natural lactones or potentially pharmaceutical compounds might be useful for organic chemists and pharmacists.

Volatile amphibian pheromones: Macrolides from mantellid frogs from madagascar

Amphibians like water, but do they also notice volatile compounds in the air? Yes, they do. Macrolides, such as phoracantholide-J (see picture; upper right structure) or the newly discovered natural product gephyromantolide-A (left structure), are used for communication by mantelline frogs from Madagascar. Copyright

Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications

Enzymatic acylation is commonly used for the kinetic resolution of alcohols and amines. The simple acyl group introduced during the enzymatic reaction is usually removed or replaced by another group. Retention of more complex acyl moieties as part of the target structures would be a more efficient strategy. We have studied the enantioselective acylation of a model alcohol substrate, 1-phenylethanol, with vinyl esters bearing various functionality on the acyl moieties in the presence of three lipases (Candida antarctica, Candida rugosa and Burkholderia cepacia) frequently used in organic synthesis. C. antarctica lipase is the most versatile lipase for this type of biotransformations. We applied this strategy to the synthesis of a protein kinase C ligand and a natural product, phoracantholide.

New silicon-mediated ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones

Silicon nucleophilic β-addition to various 2-cycloalkenones, followed ultimately by mild and rapid α-alkylation of the corresponding cycloalkanone enolates using diverse epoxides and BF3·OEt2, produces useful γ-lactols and γ-hydroxyketones. Hypervalent iodine-promoted oxidative fragmentation then yields regiospecifically unsaturated, 3-atom ring expanded, 8-10 membered homoallylic lactones with good control of alkene geometry.

New synthetic methodology for ring expansion of n-sized conjugated cycloalkenones into homoallylic n+3 lactones: Three-step synthesis of fragrant phoracantholide

Under the influence of Lewis acidic boron trifluoride-diethyl etherate, epoxides are activated sufficiently to undergo rapid nucleophilic opening by ketone enolate ions at -78°C, forming useful γ-lactols. Application of this protocol to n+3 ring expansion features one-flask, multicomponent, sequential reactions. (C) 2000 Elsevier Science Ltd.

Catalytic enantioselective synthesis of macrolides via asymmetric alkylation

Catalytic enantioselective syntheses of the macrolides (R)-(-) phoracantholide and (R)-(+) lasiodiplodin have been achieved. Stereochemistry was introduced in using an arene chromium tricarbonyl derived catalyst, which mediated the enantioselective additi

Direct synthesis of keto nitroaliphatics via retro-Henry reaction of cyclic 2-nitroalcohols by anhydrous copper sulfate adsorbed on silica gel. A short synthesis of (±)-phoracantholide I

It has been observed that anhydrous CuSO4 adsorbed on silica gel effects the C-C bond cleavage between the hydroxy group and the nitro group of 2-nitroalcohols. In the case of 2-nitrocyclohexanols, the products are RCO(CH2)4/su

Nature-like odorants by stereoselective ring enlargement of cyclohexanone and cyclododecanone

Both enantiomers of muscolide (3a/b), (R)-(-)-phoracantholide I [(R)-3c] and the homologous (9R)-(-)-9-tetradecanolide [(R)-3d) were synthesized by ring enlargement of cyclohexanone (6c) and cyclododecanone (6a). The ring-enlargement sequence was improved by oxidation of 9/10 with ruthenium tetroxide and reduction of 8 using catecholborane.