132969-71-2

Upstream product

• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 123558-64-5 N-(4-methoxybenzyl)-2,2,2-trichloroacetamide 
• 350848-02-1 2-[(4-methoxybenzyl)oxy]-3-nitropyridine 
• 56599-24-7 p-methoxybenzyl trichloroacetate 
• 127866-65-3 5-[(4-methoxybenzyl)sulfanyl]-1-phenyl-1H-tetrazole 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 185203-71-8 methyl (S)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate 
• 267236-35-1 (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene 
• 1174752-30-7 1-methoxy-4-((R)-(-)-2-methylbutoxymethyl)benzene 
• 527743-00-6 4-methyl-benzenesulfonic acid (S)-3-(4-methoxy-benzyloxy)-2-methyl-propyl ester 
• 914641-63-7 1-methoxy-4-([(2R)-2-methyl-3-butenyl]oxymethyl)benzene 
• 1322669-25-9 C₁₃H₂₀O₃ 
• 1322669-19-1 C₂₉H₃₈O₃Si 
• 1037197-61-7 (+)-tert-butyl(((2S,3S,4S)-6,6-dibromo-1-((4-methoxybenzyl)-oxy)-2,4-dimethylhex-5-en-3-yl)oxy)dimethylsilane 
• 200341-81-7 1-[(2S,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-triethylsilanyl-hex-5-ynyloxymethyl]-4-methoxy-benzene 
• 200341-76-0 2,2-Dimethyl-propionic acid (2S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester 
• 200341-80-6 (+)-tert-butyl(((2S,3S,4S)-6,6-dibromo-1-((4-methoxybenzyl)-oxy)-2,4-dimethylhex-5-en-3-yl)oxy)dimethylsilane 
• 398518-77-9 (2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid 
• 200341-74-8 2,2-Dimethyl-propionic acid (2S,3R,4S)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester 
• 200341-78-2 (2S,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol 

Relevant academic research and scientific papers

Synthesis of the C9-C25 Subunit of Spirastrellolide B

The synthesis of the C9-C25 subunit of the marine natural product spirastrellolide B is reported. The key synthetic features included the union of the two key fragments 5 and 6 via a Suzuki-Miyaura coupling reaction and a late-stage, one-pot sequential de

Stereoselective Synthesis of the C1-C22 Carbon Framework of (-)-Amphidinolide K

Two stereoselective routes to the C7-C22 subunit of amphidinolide K are disclosed. Jacobsen's hydrolytic kinetic resolution and Sharpless' asymmetric dihydroxylation reactions have been employed for the construction of the tetrahydrofuran ring. The C10-C1

Synthetic studies toward the total synthesis of tautomycetin

The studies culminating in the synthesis of two large subunits of tautomycetin are described. The first one, fragment C1-C12 that has an anti-1,3-dimethyl system and a terminal diene unit, was accomplished in 10 linear steps in 7.4% overall yield. The second one, fragment C13-C25 which bears the sensitive anhydride framework and the majority of the stereogenic centers, was prepared in 13 linear steps (longest sequence) in 8% overall yield. Among the key transformations used, a regioselective epoxide opening, a Pd-catalyzed addition of terminal alkyne to acceptor alkyne, a Mukaiyama aldol reaction, a Yamaguchi esterification, and a homemade mild di-esterification can be cited. The chosen strategies allowed good yields, stereoselectivity, reproducibility, and scalability for several important intermediates.

Leptolyngbyolides, Cytotoxic Macrolides from the Marine Cyanobacterium Leptolyngbya sp.: Isolation, Biological Activity, and Catalytic Asymmetric Total Synthesis

Four new macrolactones, leptolyngbyolides A–D, were isolated from the cyanobacterium Leptolyngbya sp. collected in Okinawa, Japan. The planar structures of leptolyngbyolides were determined by extensive NMR studies, although complete assignment of the abs

Formal synthesis of tirandamycin B

A formal synthesis of tirandamycin B is described. The key intermediate is synthesized by Marshall allenyl zinc method, litiofuran coupling, and Achmatowicz reaction to construct the bicyclic core of tirandamycin B.

Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers

A total synthesis of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3′/C4′, a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A.

Synthetic Studies toward the C32-C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36-C42 Subunit

The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an α,β-unsaturated δ-lactone followed by α-hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the 1H and 13C NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit. (Chemical Equation Presented).

Jatrophane diterpenes: Preparation of the western fragment of pl-3

Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl-3 starting from (1R,5S)-bicyclo[3.2.0]hept- 2-en-6-one is described. Key steps in the sequence include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the installation of the northern side chain through the addition of a lithiated vinyl bromide. The overall efficiency of the route is increased by taking advantage of latent symmetry. The synthesis of the western fragment of Pl-3 is developed by taking advantage of the latent symmetry in an intermediate; both enantiomers are thus converted into the desired substrate. Key steps of the synthesis include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the addition of a vinyllithium species to the completed cyclopentane moiety of the natural product.

Prediction and determination of the stereochemistry of the 1,3,5-trimethyl-substituted alkyl chain in verucopeptin, a microbial metabolite

For the prediction of the relative stereochemistry of 1,3-dimethyl substitution in alkyl chains, a simple approach based on 1H NMR data was recently proposed; Δδ values of methylene protons located between methyl-substituted methine carbons can

Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic etnangien by a flexible coupling strategy based on hetero-bis-metallated alkenes

An efficient procedure for the concise synthesis of hetero-bis-metallated alkenes as useful building blocks for the modular access to highly elaborate polyenes and stabilized analogues is reported. By applying these bifunctional olefins in convergent Stille/Suzuki-Miyaura couplings, novel, carefully selected side chain analogues of the potent RNA polymerase inhibitor etnangien were synthesized by a modular late stage coupling strategy and evaluated for antibacterial and antiproliferative activities. The Royal Society of Chemistry 2013.