132297-26-8

Upstream product

• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 89-86-1 4-hydroxysalicylic acid 
• 67-56-1 methanol 
• 122005-12-3 2,4-di-O-tert-butyldimethylsiloxybenzaldehyde 

Downstream Products

• 132260-53-8 N,N-diethyl 2,4-bis<(tert-butyldimethylsilyl)oxy>benzamide 
• 132260-55-0 methyl 4,6-dihydroxy-2-iodobenzoate 
• 132260-57-2 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoic acid 
• 132260-56-1 methyl 4,6-bis<<(2-methoxyethoxy)methyl>oxy>-2-iodobenzoate 
• 132260-54-9 N,N-diethyl-4,6-bis<(tert-butyldimethylsilyl)oxy>-2-iodobenzamide 
• 17924-92-4 zearalenone 
• 1428945-31-6 2,4-bis(dimethyl(1,1-dimethylethyl)silyloxy)-N,N-dimethylbenzamide 
• 1428945-42-9 (E)-6-(1-butenyl)-2,4-dihydroxybenzoic acid s-butyl ester 
• 1428945-41-8 (E)-6-(1-butenyl)-2,4-dihydroxybenzoic acid methyl ester 
• 1428945-40-7 (E)-6-(1-butenyl)-2,4-bis(dimethyl(1,1-dimethylethyl)silyloxy)-N,N-diethylbenzamide 
• 1428945-39-4 C₉H₁₀O₂ 
• 1428945-38-3 (E)-2,4-dihydroxy-6-(1-propenyl)benzoic acid methyl ester 
• 1428945-36-1 2,4-bis(dimethyl(1,1-dimethylethyl)silyloxy)-N,N-diethyl-6-(1-propenyl)benzamide 
• 1428945-35-0 (E)-2,4-bis(dimethyl(1,1-dimethylethyl)silyloxy)-N,N-dimethyl-6-(1-propenyl)benzamide 

Relevant academic research and scientific papers

The first total synthesis of (±)-napyradiomycin A1

(±)-Napyradiomycin A1 has been stereoselectively synthesized through a tandem Michael-Dieckmann type reaction and the introduction of a side chain and two chlorine atoms onto the pyranonaphthoquinone core.

An efficient one-pot oxidative esterification of aldehydes to carboxylic esters using B(C6F5)3-TBHP

A simple and efficient protocol for oxidative esterification of diverse aldehydes with alcohols was accomplished with tert-butyl hydroperoxide and 1 mol % of tris(pentafluorophenyl)borane [B(C6F5)3] to generate the corresponding esters in good to excellent yields. The present protocol represents compatibility with wide range of functional groups as well as exceptional tolerance toward acid labile protecting groups such as TBDPS, TBDMS, acetonide, and Boc.

Synthesis of the 2-methylene analogue of the HRV 3C protease inhibitor thysanone (2-carbathysanone)

The Human Rhinovirus (HRV) is the major aetiological agent for the common cold, for which only symptomatic treatment is available. HRV maturation and replication is entirely dependent on the activity of a virally encoded 3C protease that represents an attractive target for the development of therapeutics to treat the common cold. Herein we report the synthesis and biological evaluation of the 2-methylene analogue of the HRV 3C protease inhibitor (-)-thysanone (1) namely 2-carbathysanone (2), in an attempt to decipher the structural features in the natural product that are responsible for the 3C protease activity. 2-Carbathysanone (2) (and related analogues (±)-cis-23, (±)-cis-30, (±)-31) did not inhibit HRV 3C protease, indicating that the lactol functionality present in (-)-thysanone (1) is a critical structural feature required for inhibition.

Zearalenone mimics: Synthesis of (E)-6-(1-Alkenyl)-substituted β-resorcylic acid esters

Two versatile strategies for the synthesis of mimics of the Fusarium mycotoxin zearalenone (1) have been developed. Optimized preparation of (E)-6-(1-alkenyl) substituted β-resorcylic acid esters was realized via ortho-directed lithiation of variable substrates combined with allylation/isomerization or via formylation/Schlosser-Wittig olefination using different protective group patterns. Spontaneous decarboxylation of (E)-6-(1-alkenyl) substituted β-resorcylic acids indicated the influence of this substituent on the chemical behavior of these compounds. These mimics were already used for the development of optimized standard protocols for the synthesis of phase II metabolites of ZEN (glucosides, glucuronides), and further applications (i.e., sulfate conjugates) are still under investigation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Synthesis of β-Resorcylic Macrolides via Organopalladium Chemistry. Application to the Total Synthesis of (S)-Zearalenone

The β-resorcyclic macrolides are a class of naturally occurring 12- and 14-membered macrolides.Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest.In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct β-resorcylic macrolides.The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones.This methodology was then used to prepare (S)-zearalenone (1).