35588-79-5

Upstream product

• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 23326-27-4 Methyl 2-butynoate 

Downstream Products

• 27948-30-7 (Z)-3-methyl-5-phenyl-pent-2-en-4-ynoic acid methyl ester 
• 1208610-21-2 methyl 4-propyl-6-phenylhex-3(E)-5-ynoate 
• 1418035-98-9 C₁₇H₁₆O₄ 
• 37428-58-3 (E)-β-iodocrotyl alcohol 
• 144175-90-6 methyl 4-hydroxy-3-methyl-4-phenyl-(E)but-2-enoate 
• 405150-67-6 (2E,4E,6S,7S,8R,9S,10E)-methyl 7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienoate 
• 1264272-21-0 C₁₃H₁₈O₂ 

Relevant academic research and scientific papers

Design and biological evaluation of synthetic retinoids: Probing length vs. stability vs. activity

All trans-retinoic acid (ATRA) is widely used to direct the differentiation of cultured stem cells. When exposed to the pluripotent human embryonal carcinoma (EC) stem cell line, TERA2.cl.SP12, ATRA induces ectoderm differentiation and the formation of neuronal cell types. We report in this study that novel polyene chain length analogues of ATRA require a specific chain length to elicit a biological responses of the EC cells TERA2.cl.SP12, with synthetic retinoid AH61 being particularly active, and indeed more so than ATRA. The impacts of both the synthetic retinoid AH61 and natural ATRA on the TERA2.cl.SP12 cells were directly compared using both RT-PCR and Fourier Transform Infrared Micro-Spectroscopy (FT-IRMS) coupled with multivariate analysis. Analytical results produced from this study also confirmed that the synthetic retinoid AH61 had biological activity comparable or greater than that of ATRA. In addition to this, AH61 has the added advantage of greater compound stability than ATRA, therefore, avoiding issues of oxidation or decomposition during use with embryonic stem cells.

Step-economic synthesis of (+)-crocacin C: A concise crotylboronation/[3,3] -sigmatropic rearrangement approach

The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.

SYNTHETIC RETINOIDS FOR CONTROL OF CELL DIFFERENTIATION

The present invention relates to synthetic retinoid compounds of formula (I) and their use in the control of cell differentiation or apoptosis.

Palladium-catalyzed alkoxycarbonylation of (Z)-2-en-4-yn carbonates leading to 2,3,5-trienoates

Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with

Total synthesis of (-)-ascochlorin via a cyclobutenone-based benzannulation strategy.

The application of a convergent benzannulation strategy in an efficient synthesis of (-)-ascochlorin is described.

Total synthesis of (+)-crocacin C.

The first asymmetric synthesis of (+)-crocacin C (3) is described which served to confirm the absolute configuration of this compound. The key step in the sequence was the stereoselective assembly of the (E,E)-diene amide side chain by a Stille cross-coup

Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics

1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the γ position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes.The nature of the substituents is crucial for this diastereoselection, a ?-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.

A highly efficient synthesis of (Z) γ-iodo allylic alcohols

The reaction of (Z) Methy-β-iodo propenoate with diisobutylaluminium hydride and subsequent reaction with a Grignard reagents allows the synthesis of (Z) γ-iodo allylic alcohols in a very easy way. (Chemical Equation Presented).