111900-41-5

Upstream product

• 75950-25-3 (R)-5-Methyl-3-(1-phenylselanyl-tetradecyl)-5H-furan-2-one 
• 89448-53-3 5-Methyl-3-(1-phenylselanyl-tetradecyl)-5H-furan-2-one 
• 25966-39-6 3-bromo-5-methyldihydrofuran-2(3H)-one 
• 75938-43-1 4-methyl-2-(methylthio)-γ-butyrolactone 
• 75938-46-4 3-(1-Hydroxy-tetradecyl)-5-methyl-5H-furan-2-one 
• 75938-44-2 3-(1-Hydroxy-tetradecyl)-5-methyl-3-methylsulfanyl-dihydro-furan-2-one 
• 75938-48-6 3-(1-Hydroxy-tetradecyl)-3-methanesulfinyl-5-methyl-dihydro-furan-2-one 
• 75975-08-5 (4S,5R)-5-Methyl-4-phenylselanyl-3-tetradec-(E)-ylidene-dihydro-furan-2-one 
• 75938-47-5 Methanesulfonic acid 1-(5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-tetradecyl ester 
• 112-71-0 1-Bromotetradecane 
• 84458-94-6 2-Phenylsulfanyl-hexadecanoic acid ethyl ester 
• 84458-96-8 (4R,5R)-4-Hydroxy-5-methyl-3-phenylsulfanyl-3-tetradecyl-dihydro-furan-2-one 
• 84458-95-7 2-(2-Acetoxy-1-hydroxy-propyl)-2-phenylsulfanyl-hexadecanoic acid ethyl ester 
• 78301-20-9 <(+/-)-(3E,4α,5α)>-4-hydroxy-5-(iodomethyl)-3-tetradecylidenetetrahydro-2-furanone 

Relevant academic research and scientific papers

Synthesis of Optically Active Litsenolide C

Lithium enolate, derived from alkyl 2-(phenylthio)alkanoate with lithium diisopropylamide, reacted with aldehyde in the presence of diethylaluminum chloride to give alkyl 2-phenylthio-2-alkyl-3-hydroxyalkanoate, which was converted to 2-alkylidene-3-hydro

A SHORT STEREOSELECTIVE SYNTHESIS OF (+/-)-LITSENOLIDES C1 AND C2.

A five-step synthesis of the above substances from ethyl phenylthioacetate and 1-bromotetradecane is described.

The Total Synthesis of Lauraceae Lactones: Obtusilactones, Litsenolides, and Mahubanolides

The total synthesis of obtusilactones (1a,b, 2a,b), mahubanolides (1c, 2c), epilitsenolides (5b, 6b), and dihydromahubanolides (4c, 5c, 6c) is described.The enolates derived from the α-phenylselenenyl esters (17a-c) were used as acrylate α-anion synthons; aldol addition to propargylaldehyde, followed by oxidation to the selenoxide and elimination, furnished the isomeric acetylenic esters 20a-c and 21a-c.In a similar manner, aldol addition to acrolein followed by oxidation/elimination yielded olefinic esters 18b,c and 19b,c.The acetylenic esters were saponified, and the corresponding carboxylic acids were converted by either mercuric ion-catalyzed or bicarbonate-catalyzed lactonization to the obtusilactones (1a,b, 2a,b) and mahubanolides (1c, 2c).The olefinic esters were saponified, and the corresponding carboxylic acids lactonized to γ-substituted lactones (30b,c, 32b,c 32c) by treatment with either phenylselenenyl chloride or iodine.The epilitsenolides (5b, 6b) and dihydromahubanolides (5c, 6c) were then obtained by treating the substituted γ-lactones with tri-n-butyltin hydride.Homogeneous catalytic hydrogenation (Rh(PPh3)3Cl) of isomahubanolide (2c) gave a mixture of dihydromahubanolides 4c and 6c.

SYNTHESIS OF (+/-)-LITSENOLIDE C1

The β-hydroxy-γ-methyl-α,β'-unsaturated-γ-lactone, litsenolide C1, was synthesized in a highly stereoselective approach.