65371-43-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 18, p. 2543, 1977 DOI: 10.1016/S0040-4039(01)83815-6

Upstream product

• 121402-78-6 4,5-dihydro-4,4-dimethyl-5-phenylsulfoxymethyl (3H)-furan-2-(one) 
• 7796-72-7 ethyl 3,3-dimethylpent-4-enoate 
• 66476-86-6 ethyl 3,3-dimethyl-4-pentynoate 
• 67099-40-5 3,3-dimethyl-4-pentynoic acid 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 105-53-3 diethyl malonate 
• 7796-73-8 3,3-dimethylpent-4-enoic acid 
• 65371-41-7 5-iodomethyl-4,4-dimethyltetrahydrofuran-2-one 
• 556-82-1 3-methyl-2-buten-1-ol 
• 78984-86-8 4,4-dimethyl 5-bromomethyl-γ-butyrolactone 
• 121402-77-5 4,4-dimethyl 5-thiophenoxymethyl-γ-butyrolactone 

Relevant academic research and scientific papers

Pheromone synthesis. Part 264: Synthesis of the core 3-oxabicyclo[3.3.0]octane structures of gomadalactones A, B and C, the components of the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca

The core bicyclic cyclopentanelactone structures of gomadalactones A, B and C with α-hydroxyketone system were synthesized from (R)-pulegone, employing deconjugation of an α,β-unsaturated lactone as the key step. Comparison of the CD spectra of the synthetic compounds with those of the natural products confirmed the absolute configuration of the natural pheromone components as proposed in 2007. X-ray crystallographic analysis of the model compound of gomadalactone B core structure was carried out.

A highly active diradical cobalt(iii) catalyst for the cycloisomerization of alkynoic acids

The first cobalt-catalysed cycloisomerisation of alkynoic acids is reported, thanks to the design of a well-defined diradical cobalt(iii) catalyst, in the absence of any additives. The high efficiency, regioselectivity and chemoselectivity are comparable to those of noble metal-based systems. The unique reactivity might be attributed to second coordination sphere effects.

Intramolecular cyclization of γ-acetylenic acids using dendrimer-encapsulated Pd2+ catalysts

Polyamine dendrimer-encapsulated Pd2+ catalysts were prepared by complexation of PdCl2 with internal tertiary amino groups of the dendrimer. The fifth-generation Pd2+ dendrimer catalyst showed cooperative catalysis between Pd2+ species and the internal nanocavity consisting of regularly arranged tertiary amino groups to promote the intramolecular cyclization of γ-acetylenic acids efficiently.

Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between AuI and AuIII

ω-Acetylenic acids, substituted or not at their acetylenic end, could be efficiently cyclized to γ- or δ-alkylidene lactones in the presence of AuCl and K2CO3. In contrast AuCl3 led to lactone dimers, probably through cycl

FACILE SYNTHESIS OF 3,4-DIHYDRO-4,4-DIMETHYL-2H-PYRAN-2-ONE VIA PALLADIUM CATALYZED TERMINAL OXIDATION OF 3,3-DIMETHYL-4-PENTENOATES

Selective terminal oxidation of 3,3-dimethyl-4-pentenoates does occur under chloride-free Wacker conditions in AcOH to give 5-acetoxy-3,3-dimethyl-4-pentenoates (7) and their analogues (2,8) in good yields.Successive cyclization of 7 and 8 at vapor phase pyrolysis on SiO2 affords 3,4-dihydro-4,4-dimethyl-2H-pyran-2-one (1).

STEREOSPECIFIC SYNTHESIS OF CIS-2-ALKENYLCYCLOPROPANE CARBOXYLIC ACIDS; A TOTAL SYNTHESIS OF (+/-)-CIS-CHRYSANTHEMIC ACID

A stereospecific route to cis-2,2-dimethyl-3-alkenyl-cyclopropanecarboxylic Acids is illustrated by a total synthesis of (+/-)-cis-Chrysanthemic Acid (11).The key step consists of an alicyclic Claisen rearrangement of O-silyl enolates derived from appropriately substituted (Z)-4-hexen-6-olides .

Synthesis of 4-Penten-4-olides (γ-Methylene-γ-butyrolactones) via 4-Pentenoic Acids

4-Penten-4-olides (γ-Methylene-γ-butyrolactones) 7 are easily accessible starting from allylic alcohols 1, which on ortho ester Claisen rearrangement and hydrolytic work-up furnish 4-pentenoic acids 5.The latter on iodolactonization and hydrogen iodide elimination by means of 1,8-diazabicycloundec-7-ene (DBU) furnish 7, in good over-all yield and with variable substitution patterns. - Iodolactonization under kinetic control shows moderate 1,2- or 1,3-asymmetric induction (3:1 and ca. 2:1, respectively).The composition of the iodolactone mixtures 6 as well as the individual relative configurations are deduced from 1H and 13C NMR data. - Similary, the spirobipentenolide 13 is obtained starting from diethyl diallylmalonate (9) via 11 resulting from ester iodocyclization.