41891-54-7Relevant articles and documents
Modular Total Synthesis of iso-Archazolids and Archazologs
Dedenbach, Simon,Menche, Dirk,Rivière, Solenne,Ruiz, Johal,Scheeff, Stephan
, p. 10190 - 10223 (2021/08/16)
Full details on the design, development, and successful implementation of suitable synthetic strategies directed toward the total synthesis of iso-archazolids and archazologs are reported. Both a biomimetic and a multistep total synthesis of iso-archazolid B, the most potent and least abundant archazolid, are described. The bioinspired conversion from archazolid B was realized by a high-yielding 1,8-Diazabicyclo[5.4.0]undec-7-ene catalyzed one-step double-bond shift. A highly stereoselective total synthesis was accomplished in 25 steps, involving a sequence of highly stereoselective aldol reactions, an efficient aldol condensation to forge two elaborate fragments, and a challenging ring-closing metathesis macrocyclization with an unusual Stewart-Grubbs catalyst. These strategies proved to be generally useful and could be successfully implemented for the preparation of three novel iso-archazolids as well as five novel archazologs, lacking the thiazole side chain. A wide variety of further archazolids and archazologs may now be targeted for exploration of the promising anticancer potential of these polyketide macrolides.
Synthesis of apo-13- and apo-15-lycopenoids, cleavage products of lycopene that are retinoic acid antagonists
Narayanasamy, Sureshbabu,Sun, Jian,Pavlovicz, Ryan E.,Eroglu, Abdulkerim,Rush, Cassandra E.,Sunkel, Benjamin D.,Li, Chenglong,Harrison, Earl H.,Curley, Robert W.
, p. 1021 - 1029 (2017/05/17)
Consumption of the tomato carotenoid, lycopene, has been associated with favorable health benefits. Some of lycopene's biological activity may be due to metabolites resulting from cleavage of the lycopene molecule. Because of their structural similarity to the retinoic acid receptor (RAR) antagonist, β-apo-13-carotenone, the "first half" putative oxidative cleavage products of the symmetrical lycopene have been synthesized. All transformations proceed in moderate to good yield and some with high stereochemical integrity allowing ready access to these otherwise difficult to obtain terpenoids. In particular, the methods described allow ready access to the trans isomers of citral (geranial) and pseudoionone, important flavor and fragrance compounds that are not readily available isomerically pure and are building blocks for many of the longer apolycopenoids. In addition, all of the apo-11, apo-13, and apo-15 lycopenals/lycopenones/lycopenoic acids have been prepared. These compounds have been evaluated for their effect on RAR-induced genes in cultured hepatoma cells and, much like β-apo-13-carotenone, the comparable apo-13-lycopenone and the apo-15-lycopenal behave as RAR antagonists. Furthermore, molecular modeling studies demonstrate that the apo-13-lycopenone efficiently docked into the ligand binding site of RARα. Finally, isothermal titration calorimetry studies reveal that apo-13-lycopenone acts as an antagonist of RAR by inhibiting coactivator recruitment to the receptor.
METHOD FOR MANUFACTURING PHOSPHONOCROTONIC ACID DERIVATIVE
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Paragraph 0143-0145, (2014/03/24)
Provided is a method of manufacturing a high quality phosphonocrotonic acid derivative. The present invention is a method of manufacturing a compound represented by the following Formula (3) by reacting a compound represented by the following Formula (1) with a compound represented by the following Formula (2), which comprises a treatment process using an acid or base. [in the formula, R1 represents a C1-6 linear or branched alkyl group that may be substituted by a C6-10 aryl group, a C2-6 linear or branched alkenyl group that may be substituted by a C6-10 aryl group, a C2-6 linear or branched alkynyl group that may be substituted by a C6-10 aryl group, or a C6-10 aryl group, R2 represents a hydrogen atom, or a C1-6 linear or branched alkyl group that may be substituted by a C6-10 aryl group, R3 represents a C1-6 linear or branched alkyl group, a C6-10 aryl group, or a halogen atom, and X represents a halogen atom, and multiple R1s may be the same or different].
