111114-35-3

Upstream product

• 111114-34-2 triphenyl(1-propionylethyl)phosphonium bromide 
• 603-35-0 triphenylphosphine 
• 1754-88-7 ethylenetriphenylphosphorane 
• 3740-01-0 <1-Trimethylsilyl-ethyl>-triphenyl-phosphoniumiodid 
• 96-22-0 pentan-3-one 
• 815-52-1 2-bromopentan-3-one 
• 123-62-6 propionic acid anhydride 
• 82294-33-5 1-trimethylsilyl ethylene triphenylphosphorane 
• 16844-98-7 trimethylsilyl propionate 
• 51314-22-8 C₂₁H₁₉O₂P 

Downstream Products

• 129083-11-0 1-Hydroxy-2-methyl-4-(triphenyl-λ⁵-phosphanylidene)-pentan-3-one 
• 350246-34-3 (2R,4E)-1-(tert-Butyldiphenylsiloxy)-2,5-dimethyl-4-octen-6-one 
• 350246-24-1 (2R,6S,4E)-6-Benzyloxymethyloxy-2,5-dimethyl-4-octen-1-al 
• 350246-37-6 (2R,6S,4E)-6-Benzyloxymethyloxy-2,5-dimethyl-4-octen-1-ol 
• 350246-35-4 (2R,6S,4E)-1-(tert-Butyldiphenylsiloxy)-2,5-dimethyl-4-octen-6-ol 
• 350246-36-5 (2R,6S,4E)-6-Benzyloxymethyloxy-1-(tert-butyldiphenylsiloxy)-2,5-dimethyl-4-octene 
• 350246-38-7 (8R,8aS)-6-((E)-(2R,6S)-6-Benzyloxymethoxy-1-hydroxy-2,5-dimethyl-oct-4-enyl)-8-hydroxy-8-methyl-hexahydro-indolizin-7-one 
• 350246-39-8 (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done 
• 350246-40-1 (7S,8R,8aS,6E)-7,8-Dihydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizidine 
• 72522-40-8 (4RS,6SR,7SR)-Serricornin 
• 72598-35-7 (-)-serricornin 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 

Relevant academic research and scientific papers

The synthesis of (+)-Allopumiliotoxin 323B′

This paper describes the synthesis of (+)-allopumiliotoxin 323B′ (1) using the intramolecular [3 + 2]-cyclo-addition reaction of the (Z)-N-alkenylnitrone 4. This synthesis began with (R)-tert-butyl-3-hydroxy-pent-4-enoate [(R)-13] which was obtained by enzymatic resolution with Amano PS lipase. A series of manipulations gave intermediate 17 and in situ coupling with 4-benzoyloxybutanal lead to the (Z)-N-alkenylnitrone 4 which underwent an intramolecular [3 + 2]-cycloaddition reaction to give the isoxazolidine 3 as the major cycloadduct. Isoxazolidine 3 provided the piperidinone 24 which upon diastereofacial selective addition of MeMgBr gave the required tertiary alcohol 25. Formation of the indolizidine core 2 was achieved by an intramolecular SN2 reaction. The side chain was assembled from a Wittig reaction between the phosphorane 8 and the enantiomerically pure aldehyde 9. Further modifications afforded the aldehyde 7 which underwent an aldol condensation with the potassium enolate of the indolizidone core 2. Dehydration gave the enone 37 which was converted into the anti-diol 38 by intramolecular hydride reduction. Finally, deprotection of the BOM protecting group gave (+)-allopumiliotoxin 323B′ (1).

Synthesis and reactions of [1-(trialkylsilyl)alkylidene]triphenylphosphoranes

Alkylidenetriphenylphosphoranes 1 react with trialkyl halosilanes 2 to afford silylated alkylidenephosphoranes 5, which can be converted to acylated alkylidenephosphoranes 8 and 10 by trimethylsilyl carboxylates 6 or carboxylic anhydrides 10. Bis(acylalkylidenephosphoranes) 13-15 are available from 5 and bis(trimethylsilyl) dicarboxylates 12 or cyclic or polymeric anhydrides 16, 17.

Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes

Chiral synthesis of (-)-serricornin by using palladium-catalyzed stereoselective hydrogenolysis of the alkenyloxirane to the homoallylic alcohol with formic acid as a key step was carried out.

A new synthesis of α-β-unsaturated ketones

α,β-unsaturated ketones have been obtained by thermolysis of δ-hydroxy β-keto triphenylphosphoranes prepared from the corresponding β-keto phosphoranes.

Pheromones, 65. - Identification of the Volatile Components of the Mandibular Gland Secretion of the Ant Manica rubida: Structure Elucidation, Synthesis, and Absolute Configuration of Manicone

By means of gas chromatography and mass spectrometry, manicone, (4E)-4,6-dimethyl-4-octen-3-one (1), was identified as the main component of the mandibular gland secretion of the ant Manica rubida.In addition the presence of homomanicone (2), bishomomanicone (3), normanicone (7), and a few aliphatic aldehydes and ketones was also evident in the gland.Racemic 1, 2, and 7 and optically active dihydromanicone (4), were synthesized.The (S) configuration of 1 was determined by complexation gas chromatography, on a chiral phase, of 4 as well as of the hydrogenation products of racemic and natural 1.

Synthesis of indolizidines related to the carditonic pumiliotoxin a alkaloids

A method of making dendrobatid alkaloids with the formula STR1 in which A is either CH3 or H, and n is an integer from 1-9, and R is CH2 OH, CHO, STR2 and R1 and R2 are alkyl groups; and the use of such alkaloids to treat cardiovascular illness.