63215-85-0

Usage

Uses

Used in the Food and Beverage Industry:
(R)-4-methylhex-5-enal is utilized as a flavoring agent to impart a unique, fruity, and green taste to a wide range of food and beverages. Its natural and fresh aroma enhances the overall sensory experience of these products.
Used in the Fragrance Industry:
In perfumery, (R)-4-methylhex-5-enal is employed to add a fresh and natural aspect to fragrances. Its strong, fruity, and green odor provides a pleasant and invigorating scent, making it a popular choice for creating various types of perfumes and colognes.
Used in the Pharmaceutical Industry:
(R)-4-methylhex-5-enal also plays a significant role in the manufacturing of various pharmaceuticals. It serves as a chemical intermediate in organic synthesis, contributing to the development of new and innovative medications.
Used in the Chemical Synthesis Industry:
As a versatile chemical compound, (R)-4-methylhex-5-enal is used in the synthesis of other organic compounds. Its unique properties make it a valuable building block for creating a wide array of chemical products, further expanding its applications across different industries.

InChI:InChI=1/C7H12O/c1-3-7(2)5-4-6-8/h3,6-7H,1,4-5H2,2H3/t7-/m0/s1

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Relevant academic research and scientific papers

Total Synthesis and Structural Revision of (+)-Muironolide A

Muironolide A is a fascinating tetrachlorinated marine polyketide isolated from the sponge of Phorbas sp. Only 90 μg had been isolated, and the structure was established by nanoscale NMR techniques. Herein we report the total synthesis of the substance with the assigned structure of muironolide A, propose a revised structure based on NMR data, and complete the enantioselective total synthesis of muironolide A.

First transfer of chirality in the Fritsch-Buttenberg-Wiechell rearrangement, via zinc carbenoids: A migration with retention of configuration

Carbozincation of a metallated propargylic ether can lead to a gem bismetallic reagent with a good 1,3-diastereoselection. This latter can be relayed to a 1,4-diastereoselection, when the gembismetallic thus formed is monohalogenated to give a carbenoid which rearranges at room temperature.

Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin

Herein, we describe a biomimetic entry to (+)-3-hydroxymethylartemisinin (2) as well as to the artemisinin derivatives (+)-3-hydroxymethyl-9-desmethylartemisinin (16) and (+)-3-hydroxymethyl-9-epi-artemisinin (18), starting from the known and readily available chiral aldehyde 3 and alkyne 4. Subsequently, the synthesized compounds have been evaluated for their antimalarial activity against the drug-sensitive P. falciparum NF54 strain. All of them were inactive. In addition, they did not show any toxicity against L6 cells (a primary cell line derived from rat skeletal myoblasts). These results contribute to a better understanding of artemisinins mechanism of action.

The total synthesis of (-)-nitidasin

Nitidasin is a pentacyclic sesterterpenoid with a rare 5-8-6-5 carbon skeleton that was isolated from the Peruvian folk medicine " Hercampuri". It belongs to a small class of sesterterpenoids that feature an isopropyl trans-hydrindane moiety fused to a variety of other ring systems. As a first installment of our general approach toward these natural products, we report the total synthesis of the title compound. Our stereoselective, convergent route involves the addition of a complex alkenyl lithium compound to a trans-hydrindanone, followed by chemoselective epoxidation, ring-closing olefin metathesis, and redox adjustment.

Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin

Astellatol and nitidasin belong to a subset of sesterterpenoids that share a sterically encumbered trans-hydrindane motif with an isopropyl substituent. In addition, these natural products feature intriguing polycyclic ring systems, posing significant challenges for chemical synthesis. Herein, the evolution of our stereoselective strategy for isopropyl trans-hydrindane sesterterpenoids is detailed. These endeavors included the synthesis of several building blocks, enabling studies toward all molecules of this terpenoid subclass, and of advanced intermediates of our initial route toward a biomimetic synthesis of astellatol. These findings provided the basis for a second-generation and a third-generation approach toward astellatol that eventually culminated in the enantioselective total synthesis of (-)-nitidasin. In particular, a series of substrate-controlled transformations to install the ten stereogenic centers of the target molecule was orchestrated and the carbocyclic backbone was forged in a convergent fashion. Furthermore, the progress toward the synthesis of astellatol is disclosed and insights into some observed yet unexpected diastereoselectivities by detailed quantum-mechanical calculations are provided. Two and a half molecules: Astellatol and nitidasin are polycyclic sesterterpenoids, posing considerable challenges for synthetic chemists. In this full account, the evolution of a synthetic strategy for these and structurally related natural products is given (see scheme). The presented work includes efforts toward a biomimetic synthesis of astellatol, a successful route for the first total synthesis of (-)-nitidasin, and quantum-mechanical investigations into unexpected diastereosectivities.

Heterocycle synthesis based on allylic alcohol transposition using traceless trapping groups

Allylic alcohols undergo transposition reactions in the presence of Re 2O7 whereby the equilibrium can be dictated by trapping one isomer with a pendent electrophile. Additional ionization can occur when the trapping group is an aldehyde or ketone, thus leading to cyclic oxocarbenium ion formation. Terminating the process through bimolecular nucleophilic addition into the intermediate provides a versatile method for the synthesis of diverse oxygen-containing heterocycles. Understanding the relative rates of the steps in the sequence leads to the design of reactions which create multiple stereocenters with good to excellent levels of control.

Studies toward the total synthesis of carolacton

An efficient synthesis of the C1-C19 segment of carolacton is described, starting from d-ribose, (-)-β-citronellene and a homopropargylic alcohol, and which employs a Nozaki-Hiyama-Kishi (NHK) coupling as the key step. Other important steps are cross-metathesis and Evans aldol reactions. Georg Thieme Verlag Stuttgart New York.

Macrolides and alcohols as scent gland constituents of the Madagascan frog mantidactylus femoralis and their intraspecific diversity

Acoustic and, to a lesser degree, visual signals are the predominant means of signaling in frogs. Nevertheless, certain lineages such as the mantelline frogs from Madagascar use the chemical communication channel as well. Males possess femoral glands on the hind legs, which recently have been shown to contain volatile compounds used in communication as pheromones. Many mantelline species occur in sympatry, and so far species recognition is regarded to occur mainly by acoustic signals. The analysis of the gland constituents of Mantidactylus femoralis by GC/MS revealed the presence of volatile macrolides and secondary alcohols. The new natural products mantidactolides A (4) and B (6), as well as several methyl carbinols, were identified, and their structures were confirmed by synthesis. The analysis of individuals from different locations of Madagascar revealed the presence of two groups characterized by specific patterns of compounds. While one group contained the alcohols and mantidactolide B, the other showed specific presence of the macrolides phoracantholide I (1) and mantidactolide A (4). Genetic analysis of some individuals showed no congruence between genetic relatedness and gland constituents. Several other individuals from related species had different gland compositions. This suggests that a basic set of biosynthetic machinery might be available to a broader group of related species.

Synthetic studies toward (+)-spongidepsin

A convergent enantiomerically controlled synthetic effort toward (+)-spongidepsin is reported. The synthesis benefits from the use of readily available and inexpensive starting materials like D-mannitol and (-)-β-citronellene. Key transformations include Evans asymmetric methylation, Mitsunobu esterification, (1H-benzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (PyBOP)-mediated amide formation for the preparation of a fully functionalized acyclic precursor, and ring-closing metathesis (RCM). Copyright

The total synthesis of corallopyronin A and myxopyronin B

Leading the way: The synthesis of natural products with new biological targets is one of the driving forces for the development of new antibiotics. The synthesis of the two secondary metabolites corallopyronin and myxopyronin (see picture) have been achieved, which are prominent leads for the inhibition of bacterial RNA polymerase. Copyright