1400-44-8

Upstream product

• 861454-84-4 2-hydroxy-6-[4-(3-iodo-2-methyl-allylidene)-tetrahydro-furan-2-yl]-3,5-dimethyl-pyran-4-one 
• 51738-10-4 2,2-dibromo-1-(4-nitrophenyl)ethene 
• 846031-12-7 (+/-)-2-methoxy-3,5-dimethyl-6-(4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-tetrahydrofuran-2-yl)-4H-pyran-4-one 
• 846031-09-2 (+/-)-2-methoxy-3,5-dimethyl-6-(1-(phenylselenyl)ethyl)-4H-pyran-4-one 
• 846031-08-1 (+/-)-2-methoxy-3,5-dimethyl-6-(4-methylenetetrahydrofuran-2-yl)-4H-pyran-4-one 
• 846031-10-5 2-methoxy-3,5-dimethyl-6-vinyl-4H-pyran-4-one 
• 861454-76-4 2-[4-(3-iodo-2-methyl-allylidene)-tetrahydro-furan-2-yl]-6-methoxy-3,5-dimethyl-pyran-4-one 
• 79048-32-1 4-(tri-n-butylstannyl)nitrobenzene 
• 846031-14-9 (+/-)-2-((Z)-4-((Z)-2-bromo-3-(4-nitrophenyl)allylidene)-tetrahydrofuran-2-yl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one 
• 544-97-8 dimethyl zinc(II) 
• 1101168-58-4 (R)-2-((3E,5E)-1-hydroxy-3,5-dimethyl-6-(4-nitrophenyl)hexa-3,5-dienyl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one 

Relevant academic research and scientific papers

Convergent asymmetric synthesis of (+)-aureothin employing an oxygenase-mediated resolution step

Need an enzymatic push? The desymmetrization of α,α'-dimethoxy- γ-pyrone allows the convergent and rapid preparation of the complete carbon skeleton of (+)-aureothin (see scheme). The final step in the synthesis of the target molecule is the regiodivergen

Absolute configuration of (+)-aureothin: A toxic metabolite possessing γ-pyrone unit

The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.

Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent

Amenable to late-stage preparation of analogues, a flexible and convergent total synthesis of (±)-aureothin is presented. The strategy was based on a desymmetrization of α,α′-dimethoxy-γ-pyrone by a process combining 1,4-addition and alkylation of vinylogous enolate to stereoselectively reach the backbone of the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z dienyl motif followed by Pinner cyclization enabled the construction of the tetrahydrofuran motif while a first approach based on a late-stage oxidation was unsuccessful.

Structural fine-tuning of a multifunctional cytochrome P450 monooxygenase

AurH is a unique cytochrome P450 monooxygenase catalyzing the stepwise formation of a homochiral oxygen heterocycle, a key structural and pharmacophoric component of the antibiotic aureothin. The exceptional enzymatic reaction involves a tandem oxygenatio

Sequential asymmetric polyketide heterocyclization catalyzed by a single cytochrome p450 monooxygenase (AurH)

(Chemical Equation Presented) Two in one: In vitro biotransformations with the cytochrome P450 monooxygenase AurH from the aureothin (1) biosynthetic pathway provided direct experimental evidence that a single monooxygenase can install two C-O bonds sequentially to form a tetrahydrofuran ring. Structural elucidation of the intermediate 2 revealed the order of bond formation and the stereochemical course of this unprecedented oxygenation-heterocyclization reaction.

The biomimetic synthesis of SNF4435C and SNF4435D, and the total synthesis of the polyene metabolites aureothin, N-acetyl-aureothamine and spectinabilin

Full details of the biomimetic conversion of polyene metabolite spectinabilin (5) into the isomeric natural products SNF4435C (1) and SNF4435D (2) by a cascade of E/Z-isomerizations and electrocyclizations are reported. Additionally, short total syntheses

Stereoselective Syntheses of the Bioactive Polypropionates Aureothin, N-Acetylaureothamine, and Aureonitrile

Concise total syntheses of the bioactive polypropionates aureothin, N-acetylaureothamine, and aureonitrile are described.

A short total synthesis of aureothin and N-acetylaureothamine

(Chemical Equation Presented) The total synthesis of the nitrophenyl pyrones, (±)-aureothin and (±)-N-acetylaureothamine, starting from known 2-ethyl-6-methoxy-3,5-dimethyl-4H-pyran-4-one are described. The key steps involved in the synthesis are the cons