5730-01-8

Upstream product

• 89-82-7 pulegone 
• 89-82-7 pulegone 

Downstream Products

• 90461-82-8 Sodium; (R)-5-methyl-2-phenylsulfanyl-cyclohex-1-enolate 
• 94416-79-2 (1R,3S,4R)-4,8-epoxy-3-vinyl-p-menthan-3-ol 
• 97323-17-6 5-ref-Methyl-2-cis-hydroxy-2-(α-fluor-isopropyl)-cyclohexanon 
• 35837-05-9 (+)-(1R,3R,4S)-Δ⁸-p-Menthen-3,4-diol (5) 
• 97372-38-8 5-ref-Methyl-2-trans-hydroxy-2-(α-fluor-isopropyl)-cyclohexanon 

Relevant academic research and scientific papers

A novel synthesis of (?)-callicarpenal

Callicarpenal, isolated from the leaves of American beautyberry (Callicarpa americana) and Japanese beautyberry (Callicarpa japonica), exhibits significant mosquito bite-deterring activity and repellent activity against ticks and fire ants. The mosquito bite-deterring activity level of callicarpenal was reported to be similar to that of N,N-diethyl-m-toluamide. The novel synthesis of (?)-callicarpenal reported herein was accomplished by starting from (+)-pulegone. In our original approach, a novel Prins-type cyclization based on Meyer–Schuster rearrangement was featured as a key step.

Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids

Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.

Efforts toward the synthesis of (+)-Lyconadin A

Abstract: Synthetic efforts toward the synthesis of (+)-lyconadin A are described. B-Alkyl Suzuki coupling is utilized for combining 2-iodo cyclohexenone with the piperidine subunit. The piperidine subunit is derived from 5-bromo-3-nicotinic acid, and iod

A concise asymmetric total synthesis of (+)-fawcettimine

A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/

Biocidal Compounds from Mentha sp. Essential Oils and Their Structure–Activity Relationships

Essential oils from Greek Mentha species showed different chemical compositions for two populations of M.?pulegium, characterized by piperitone and pulegone. Mentha spicata essential oil was characterized by endocyclic piperitenone epoxide, piperitone epo

Total Synthesis of (-)-Carinatine A and (+)-Lycopladine A

An efficient synthesis of two Lycopodium alkaloids, (-)-carinatine A and (+)-lycopladine A, is achieved in eight steps. The synthesis features an intramolecular aldol reaction for assembling the 6,5-fused ring system, a subsequent Tsuji-Trost allylation for generating a quarternary carbon center, and a 6π-electrocyclization to form the pyridine ring.

The first asymmetric total synthesis of lycoposerramine-R

The first asymmetric total synthesis of lycoposerramine-R, a Lycopodium alkaloid possessing a novel skeleton, was accomplished by a strategy featuring the stereoselective intramolecular aldol cyclization giving a cis-fused 5/6 bicyclic skeleton and a new method for the construction of the pyridone ring via the aza-Wittig reaction.

Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions

The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycodine core.

A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation

In our synthetic studies toward huperzine A, a diastereoselective α′-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo[3.3.1]nonane framework in satisfactory yield.

Oxidation studies on some natural monoterpenes: Citral, pulegone, and camphene

Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C2=C3 and C6=C7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C2=C3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7- dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1- oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide derivatives, 2-(1-hydroperoxy-1-methylethyl)-5- methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl) cyclohexan-1-one, were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.