75889-47-3

Upstream product

• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 74-88-4 methyl iodide 
• 91-16-7 1,2-dimethoxybenzene 
• 214282-99-2 1-iodo-2,3-dimethoxy-4-methylbenzene 

Downstream Products

• 147807-80-5 2?hydroxy?3?methoxy?4?methylbenzaldehyde 
• 951161-56-1 2,3-dimethoxy-1-methyl-4-vinylbenzene 
• 1442465-77-1 (2E,5E)-2,5-bis(2,3-dimethoxy-4-methylbenzylidene)cyclopentanone 
• 6053-03-8 2,3-dihydroxy-4-methyl-benzaldehyde 
• 1284222-80-5 (S)-4-(2,3-dimethoxy-4-methylphenyl)pentanenitrile 
• 1284222-79-2 (S)-1-(4-iodobutan-2-yl)-2,3-dimethoxy-4-methylbenzene 
• 1284222-88-3 (S)-3-(2,3-dimethoxy-4-methylphenyl)butan-1-ol 
• 1284222-78-1 (S)-1-(but-3-en-2-yl)-2,3-dimethoxy-4-methylbenzene 
• 1027896-93-0 1-Hydroxymethyl-7-methoxy-6-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-8-ol 
• 147807-86-1 6-[1-(2,2-Diethoxy-ethylamino)-2-hydroxy-ethyl]-2-methoxy-3-methyl-phenol 
• 147807-88-3 N-(2,2-Diethoxyethyl)-N-<1-(2-benzyloxy-3-methoxy-4-methylphenyl)-2-benzyloxyethyl>toluene-p-sulfonamide 
• 147807-89-4 8-Benzyloxy-1-benzyloxymethyl-7-methoxy-6-methyl-2-(p-tolylsulfonyl)-1,2-dihydroisoquinoline 

Relevant academic research and scientific papers

Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A?F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation

Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt-catalyzed hydrovinylation as the chirogenic step. Other noteworthy C?C bond forming transformations include diastereoselective Lewis acid-mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4-methyl-styrene the anti-tubercular agent (+)-erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti-inflammatory activity (inhibition of LPS-induced NF-κB activation) as a natural mixture of pseudopterosins A?D or iso-pseudopterosin A, prepared by β-D-xylosylation of the synthetic aglycone.

Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control

A stereogenic center, placed at an exocyclic location next to a chiral carbon in a ring to which it is attached, is a ubiquitous structural motif seen in many bioactive natural products, including di- and triterpenes and steroids. Installation of these ce

BORON-CONTAINING SMALL MOLECULES

This invention relates to, among other items, benzoxaborole compounds and their use for treating bacterial infections.

Ethylene in organic synthesis. repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins

In this report we highlight the significant potential of ethylene as a reagent for the introduction of a vinyl group with excellent stereoselectivity at three different stages in the synthesis of a broad class of natural products, best exemplified by synt

Enantioselective synthesis of a trans-7,8-dimethoxycalamenene

trans-7,8-Dimethoxy-11,12-dehydrocalamenene, a projected intermediate for the total synthesis of marine serrulatane and amphilectane diterpenes, was efficiently synthesized. Starting from a styrene, asymmetric Rh-catalyzed hydroboration using a novel chiral P.P-bidentate ligand afforded an organoboron intermediate (93% ee) which was directly used for C-C bond formation (double homologation, Suzuki coupling). The 1,4-trans-disubstituted tetralin skeleton was selectively formed by a Friedel-Crafts-type catlonic cyclization under strictly aprotic conditions (Me2AlCl) to suppress a remarkable proton-catalyzed disproportionation via diastereoselective hydride transfer.

Total synthesis of the β-adrenergic receptor antagonist, the tetrahydroisoquinoline MY336-a and its epimer

The first total synthesis of the novel β-adrenergic receptor antagonist MY336-a 1 and its epimer 2 has been achieved from 2,3-dimethoxytoluene, by Jackson cyclisation of N-benzyl-N-tosylamido acetals, Lewis acid-mediated addition of silicon-based nucleoph

Studies on the Natural β-Adrenergic Receptor Antagonist MY336-a: Synthesis of a 3-Dehydroxymethyl Analogue

The preparation of a polysubstituted tetrahydroisoquinoline, which lacks only the 3-CH2OH group of MY336-a, is described.

Ortho Metalation Directed by α-Amino Alkoxides

The addition of aromatic aldehydes to certain lithium dialkylamides in benzene or tetrahydrofuran gave α-amino alkoxides which were ortho lithiated with excess n-butyllithium.Subsequent alkylation and hydrolysis provided ortho-substituted aromatic aldehydes via a one-pot reaction.The ortho metalation of α-amino alkoxides derived from 1- and 2-naphthaldehyde and various substituted benzaldehydes was examined.When N,N,N'-trimethylethylenediamine was used as the amine component of the α-amino alkoxide, metalation could be carried out at lower temperatures.This rate increase is due to an intramolecular TMEDA-like assisted metalation.The synthetic utility of this ortho metalation, including how varying the amine component of the α-amino alkoxide affects the regiochemistry and metalation rate, is discussed.