78592-73-1

Upstream product

• 75-24-1 trimethylaluminum 
• 927-74-2 3-Butyn-1-ol 

Downstream Products

• 88968-96-1 5-((tert-Butyldimethylsilyl)oxy)-3-methyl-2(E)-pentenoic Acid 
• 871316-21-1 5-(4-iodo-3-methyl-but-3-enylsulfanyl)-1-phenyl-1H-tetrazole 
• 527755-03-9 (4R,5S,6S)-6-[(E)-1,5-dimethylhex-1-enyl]-4-hydroxy-5-methoxycyclohex-2-enone 
• 527755-05-1 (2S,3S,4R,5R)-4-hydroxy-3-methoxy-5-methyl-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527755-11-9 (2S,3S,4R,5R)-4-hydroxy-3-methoxy-5-ethyl-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527754-86-5 (4R)-4-benzyl-3-[(3E)-3,7-dimethylocta-3-enoyl]oxazolidin-2-one 
• 527755-07-3 (2S,3S,4R,5R)-4-trimethylsilyloxy-3-methoxy-5-methyl-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527754-96-7 (4R,5S,6S)-5-methoxy-4-p-methoxybenzyloxy-6-[(E)-1,5-dimethylhex-1-enyl]cyclohex-2-enone 
• 527754-98-9 (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 
• 527754-94-5 (4S)-4-((1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl)-5,9-dimethyldeca-1,5-dien-3-one 
• 527755-39-1 (1R,3S,4S,5S,6R)-3-[(E)-1,5-dimethylhex-1-enyl]-4-methoxy-5-p-methoxybenzyloxy-7-oxabicyclo[4.1.0]heptan-2-one 
• 527755-34-6 (2S,3S,4R,5S)-2-((E)-1,5-dimethylhex-1-enyl)-3-methoxy-4-p-methoxybenzyloxy-5-methylcyclohexanone 
• 527754-99-0 (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 
• 527755-13-1 (2S,3S,4R,5R)-4-benzoyloxy-5-ethyl-3-methoxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 

Relevant academic research and scientific papers

Efficient assembly of the phomactin core via two different macrocyclization protocols.

[reaction--see text] The core structure of phomactins C and D was assembled by an efficient strategy starting from 3,4-dimethylcyclohexen-2-one. Key reactions include (1) a high yielding and highly diastereoselective Michael addition of a mixed cuprate, (

Synthesis of the C1-C13 fragment of (+)-callipeltoside A

The synthesis of the C1-C13 fragment of (+)-callipeltoside A has been achieved in 12 steps with an overall yield of 11%. Georg Thieme Verlag Stuttgart.

An efficient and stereoselective synthesis of the monomeric counterpart of marinomycin A

Equation presented The monomeric counterpart of marinomycin A, an antitumor-antibiotic marine natural product, was synthesized efficiently in 11 steps from the commercially available ethyl (R)-(-)-3-hydroxybutyrate. The strategy was highlighted by a cruci

Copper-catalyzed cross-coupling of amino acid-derived amides with (Z)-vinyl iodides: Unexpected solvent effect and preparation of plocabulin

A copper-catalyzed cross-coupling reaction of amino acid-derived amides and (Z)-vinyl iodide was studied to improve a key step in the synthesis of plocabulin, a novel microtubule destabilizer agent of marine origin. The study revealed a profound solvent effect with 1,2-dimethoxyethane (DME), which gave consistently high yields across a large variety of the amide and (Z)-vinyl iodide substrates. The protocol was successfully utilized in the preparation of plocabulin and provided a significantly improved yield.

Methyl-Shifted Farnesyldiphosphate Derivatives Are Substrates for Sesquiterpene Cyclases

New sesquiterpene backbones are accessible after biotransformation of presilphiperfolan-8β-ol synthase (BcBOT2), a fungal sesquiterpene synthase, with non-natural farnesyldiphosphates in which methyl groups are shifted by one position toward the diphosphate terminus. One of the macrocycles formed, a new germacrene A derivative, undergoes a Cope rearrangement to iso-β-elemene. Three of the new terpenoids show olfactoric properties that range from an intense peppery note to a citrus, ozone-like, and fruity scent.

Synthesis and biological evaluation of fluorinated analogues of ripostatin A

Several monocyclic derivatives of 14,14′-difluororipostatin A were prepared using a catalytic Mukaiyama aldol reaction, a ring-closing metathesis reaction and a late stage click reaction as key steps. The biological activity of the produced compounds was assessed in vivo using a panel of pathogenic microorganisms. Moderate antibiotic activity was observed for 11-OMe-ripostatin A and 11-OMe-14,14′-difluororipostatin A.

Dialkoxycarbenes in (4 + 1) Cycloadditions: Application to the Synthesis of Carotol

Dialkoxycarbenes are more reactive than NHCs and participate in many reactions including a formal (4 + 1) cycloaddition with electron-deficient dienes. We have learned to control the relative stereochemistry of the newly created chiral carbons in this pro

A Two-Component Alkyne Metathesis Catalyst System with an Improved Substrate Scope and Functional Group Tolerance: Development and Applications to Natural Product Synthesis

Although molybdenum alkylidyne complexes such as 1 endowed with triarylsilanolate ligands are excellent catalysts for alkyne metathesis, they can encounter limitations when (multiple) protic sites are present in a given substrate and/or when forcing conditions are necessary. In such cases, a catalyst formed in situ upon mixing of the trisamidomolybenum alkylidyne complex 3 and the readily available trisilanol derivatives 8 or 11 shows significantly better performance. This two-component system worked well for a series of model compounds comprising primary, secondary or phenolic -OH groups, as well as for a set of challenging (bis)propargylic substrates. Its remarkable efficiency is also evident from applications to the total syntheses of manshurolide, a highly strained sesquiterpene lactone with kinase inhibitory activity, and the structurally demanding immunosuppressive cyclodiyne ivorenolide A; in either case, the standard catalyst 1 largely failed to effect the critical macrocyclization, whereas the two-component system was fully operative. A study directed toward the quinolizidine alkaloid lythrancepine I features yet another instructive example, in that a triyne substrate was metathesized with the help of 3/11 such that two of the triple bonds participated in ring closure, while the third one passed uncompromised. As a spin-off of this project, a much improved ruthenium catalyst for the redox isomerization of propargyl alcohols to the corresponding enones was developed.

Diastereoselective Oxidative CN/CO and CN/CN Bond Formation Tandems Initiated by Visible Light: Synthesis of Fused N-Arylindolines

The synthesis of fused N-arylindolines using visible light photoredox catalysis has been developed. We previously described that photogenerated amine radical cations generate substituted indoles through an intermediate benzylic carbocation. Herein, we expand the application of this chemistry by trapping the benzylic carbocation with tethered heteronucleophiles. The reactivity of the photogenerated benzylic carbocation is explored and applied to a range of substrates with various electronic characters and ring constraints. The method described provides C-2 and C-3 fused indolines bearing a tetrasubstituted carbon stereocenter with greater than 99:1 diastereoselectivity in moderate to good yields.

Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes

A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans s