143833-82-3

Upstream product

• 74076-63-4 2-(4-methoxyphenyl)-4,7-dihydro-1,3-dioxepine 
• 193893-08-2 (R)-4-[(R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane 
• 123-11-5 4-methoxy-benzaldehyde 
• 193893-10-6 Methanesulfonic acid (R)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-ethyl ester 
• 193893-09-3 (R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-ethanol 
• 824-94-2 p-methoxybenzyl chloride 
• 143833-81-2 (Z)-4-(4-methoxybenzyloxy)but-2-en-1-ol 
• 193893-11-7 Methanesulfonic acid (1R,2R)-2,3-dihydroxy-1-(4-methoxy-benzyloxymethyl)-propyl ester 

Downstream Products

• 143833-84-5 (2S,3R)-3-azido-4-O-(4-methoxybenzyl)butan-1,2,4-triol 
• 143833-83-4 (2S,3R)-2-azido-4-O-(4-methoxybenzyl)butan-1,3,4-triol 
• 260393-74-6 (2S,3S)-4-(p-methoxybenzyloxy)-2,3-epoxybutanal 

Relevant academic research and scientific papers

Catalytic diastereoselective reduction of α,β-epoxy and α,β-aziridinyl ynones

The Noyori transfer hydrogenation of α,β-epoxy and α,β-aziridinyl ynones leads to the corresponding α,β-epoxy or α,β-aziridinyl propargylic alcohols with high reagent-controlled diastereoselectivity.

Total synthesis of (+)-amphidinolide A. Assembly of the fragments

The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of total synthesis and NMR spectroscopic analysis. Amphidinolide A possesses two skipped 1,4-diene subunits which are accessible by ruthenium-catalyzed alkene-alkyne couplings. Previous total syntheses had revealed that the reported structure was incorrect; therefore, to incorporate maximum flexibility into the synthesis, with the ultimate goal of determining the correct structure, a highly convergent approach was chosen. Furthermore, liberal use was made of catalytic asymmetric transformations to set individual stereocenters. Three different strategies were envisioned for the end game, and due to the highly convergent nature of the synthesis, all three routes disconnect to the same three key intermediates, 5, 6, and 7. Diastereomers of 6 and 7 were easily prepared by modification of the synthetic routes to allow access to multiple diastereomers of 1 for structural determination.

Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide

Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright

Ruthenium-catalyzed alkene-alkyne coupling: Synthesis of the proposed structure of amphidinolide A

The ruthenium-catalyzed alkene-alkyne coupling provides a powerful method for the synthesis of 1,4 dienes and a way to simplify synthetic strategy. The latter potential is explored in the context of a synthesis of the assigned structure of amphidinolide A

Synthesis of the first photo-triggered pro-mitosene based on FR-900482

A stereocontrolled synthesis of an eight-membered ring precursor to a photo-triggered mitosene is described. (C) 2000 Elsevier Science Ltd.

Synthetic studies on FR 900482. Synthesis of a photo-triggered pro-mitosene

A stereocontrolled synthesis of an eight-membered ring precursor to a photo-triggered mitosene is described.

Total synthesis of an enantiomeric pair of FR980482. 2. Syntheses of the aromatic and the optically active aliphatic segments

The synthesis of the aromatic segment 4 was achieved starting from commercially available 5-hydroxyisophthalic acid (6) by utilizing Claisen rearrangement of 9, bromolactonization of 12, and modified Curtius rearrangement of 16 as the key steps. Furthermore, the optically active aliphatic segments 5 and ent-5 were synthesized in enantiomerically pure forms starting with natural (2R, 3R)- and unnatural (2S, 3S)-diethyl tartrate (7 and ent-7), respectively: The synthetic scheme features epoxide formation of 26, nucleophilic epoxide opening of 27 with an azide anion, reduction of the azide function in 33 to an amine, and formation of the N-protected 1,3-oxazolidine 35.

Total synthesis of natural (+)-FR900482. 2. Efficient syntheses of the aromatic and the optically active aliphatic fragments

The synthesis of the aromatic fragment 4 was achieved starting from commercially available 5-hydroxy-isophthalic acid (6) by utilizing Claisen rearrangement of 9, bromolactonization of 12, and modified Curtius rearrangement of 16 as key steps. Furthermore, the optically active aliphatic fragment 5 was synthesized in an optically pure form starting with L-diethyl tartrate (7) by featuring epoxide formation of 26, nucleophilic epoxide opening of 27 with an azide anion, reduction of the azide function in 33 to an amine, and formation of the N-protected 1,3-oxazolidine 35.

STEREOSPECIFIC SYNTHESIS OF A RIBOSYL-DIAZEPANONE DERIVATIVE; A SYNTHETIC APPROACH FOR ELUCIDATION OF THE STEREOCHEMISTRY OF A LIPID NUCLEOSIDE ANTIBIOTIC LIPOSIDOMYCIN B

A new type of ribosyl-diazepanone derivative (23), the core ribosyl 7-membered heterocycle of the nucleoside antibiotic liposidomycin B has been synthesized using a chiral synthetic route that could offer accessibility to any of possible stereoisomers of