142860-83-1

Upstream product

• 627-27-0 homoalylic alcohol 
• 2746-25-0 p-Methoxybenzyl bromide 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 623-12-1 4-chloromethoxybenzene 
• 142860-84-2 4-(p-methoxybenzyloxy)-1,2-epoxybutane 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 167629-46-1 (p-methoxybenzyloxy)-2-hydroxybutanol 
• 167629-45-0 4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane 
• 671232-57-8 (E)-5-(4-methoxy-benzyloxy)-pent-2-en-1-al 
• 131375-69-4 5-((4-methoxybenzyl)oxy)pentanal 
• 158817-21-1 (E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol 
• 158817-23-3 (2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol 
• 1005776-31-7 (E)-ethyl-3-((2S,3S)-3-(2-(4-methoxybenzyloxy)ethyl)oxiran-2-yl)acrylates 
• 1376666-11-3 (4R,5S,E)-ethyl-5-hydroxy-7-(4-methoxybenzyloxy)-4-methylhept-2-enoate 
• 1376666-13-5 C₂₂H₃₈O₄Si 
• 1376666-15-7 C₂₂H₃₆O₄Si 
• 1376666-17-9 C₂₆H₄₂O₅Si 
• 1376666-04-4 C₂₃H₂₅F₃O₆ 
• 146986-42-7 ((2S,3S)-3-(2-(4-methoxybenzyloxy)ethyl) oxiran-2-yl)methanol 
• 794527-59-6 (2R,3S)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-oxirane-2-carbaldehyde 

Relevant academic research and scientific papers

The first stereoselective synthesis of dendrodolide A

The first stereoselective total synthesis of natural product, dendrodolide A (1) is described from readily available (R)-propylene oxide and 3-buten-1-ol as starting materials. The synthesis was achieved in 10 steps with an overall yield of 19.1%. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification, and ring-closing metathesis (RCM).

A total synthesis of spirastrellolide a methyl ester

A concise total synthesis of spirastrellolide A methyl ester (1 a, R 1=Me) as the parent compound of a series of highly cytotoxic marine macrolides is disclosed, which exploits and expands the flexibility of a synthesis plan previously developed by our group en route to the sister compound spirastrellolide F methyl ester (6 a, R1=Me). Key to success was the masking of the signature Δ15,16-bond of 1 a as a C16-carbonyl group until after the stereogenic center at C24 had been properly set by a highly selective hydrogenation of the C24 exo-methylene precursor 66. Conformational control over the macrocyclic frame allowed the proper stereochemical course to be dialed into this reduction process. The elaboration of the C16 ketone to the C15-C16 double bond was accomplished by a chemoselective alkenyl triflate formation followed by a palladium-catalyzed hydride delivery. The role of the ketone at C16 as a strategic design element is also evident up-stream of the key intermediate 66, the assembly of which hinged upon the addition of the polyfunctionalized dithiane 37 to the similarly elaborate aldehyde fragment 46. Other crucial steps of the total synthesis were an alkyl-Suzuki coupling and a Yamaguchi lactonization that allowed the Northern and the Southern sector of the target to be stitched together and the macrocyclic perimeter to be forged. The lateral chain comprising the remote C46 stereocenter was finally attached to the core region by a modified Julia-Kocienski olefination. The preparation of the individual building blocks led to some methodological spin-offs, amongst which the improved procedure for the N-O-bond cleavage of isoxazolines by zero-valent molybdenum and the ozonolysis of a double bond in the presence of other oxidation-prone functionality are most noteworthy. Preliminary biological data suggest that the entire carbon framework, that is the macrocyclic core plus the lateral chain, might be necessary for high cytotoxicity. Copyright

Total synthesis, biological evaluation of dendrodolides A–D and their analogues

A concise total synthesis of dendrodolides A–D (1–4) has been accomplished in 10 steps from commercially available (R)-propylene oxide and 3-buten-1-ol as starting materials. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification and ring-closing metathesis (RCM). In addition, a series of ester derivatives were prepared utilizing Yamaguchi esterification at the C-3 position of the dendrodolide core and screened for their efficacy against cancer cell lines.

Studies toward the Total Synthesis of the Marine Macrolide Salarin C

A convergent strategy for the synthesis of dideoxysalarin C (3) as a potential intermediate for the total synthesis of the marine macrolide salarin C (1) is described. The macrolactone core of 3 was assembled by Suzuki coupling between alkyl iodide 9 and

Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation-Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols

Starting from readily available allylglycine, a tandem hydroformylation-hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,

ANTIVIRAL COMPOUNDS

Disclosed herein are new antiviral compounds, together with pharmaceutical compositions that include one or more antiviral compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a paramyxovirus v

Regioselective and Stereospecific Copper-Catalyzed Deoxygenation of Epoxides to Alkenes

Two copper salts (Cu(CF3CO2)2 and IMesCuCl) were identified as earth-abundant, inexpensive, but effective metal catalysts together with diazo malonate for chemo-/regioselective and stereospecific deoxygenation of various epoxides with tolerance of common functional groups (alkene, ketone, ester, p-methoxybenzyl, benzyl, tert-butyldimethylsilyl, and triisopropylsilyl). In particular, the unprecedented regioselectivity allowed for the first time monodeoxygenation of diepoxides to alkenyl epoxides. Density functional theory mechanistic studies showed that the deoxygenation occurred by collapsing the free ylide, unfavoring the possible intuitive pathway via cycloreversion of possible oxetane.

Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand

A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).

Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation-lactonization approach

A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclizat

Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes

Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif.