76529-42-5Relevant articles and documents
Radical photocyclization route for macrocyclic lactone ring expansion and conversion to macrocyclic lactams and ketones
Nishikawa, Keisuke,Yoshimi, Yasuharu,Maeda, Kousuke,Morita, Toshio,Takahashi, Ichiro,Itou, Tatsuya,Inagaki, Sho,Hatanaka, Minoru
, p. 582 - 589 (2013)
A new method for the synthesis of macrocyclic lactones, lactams, and ketones, which utilizes photoinduced intramolecular radical cyclization reactions of substrates containing tethered carboxylic acids and α,β-unsaturated carbonyl moieties, has been uncovered. Photocyclization of the carboxylic acids tethered acrylate ester, which were prepared starting from the macrocyclic lactones, gave the two-carbon elongated macrocyclic lactones via decarboxylation. Similar photoreactions of carboxylic acid tethered acryl amide or α,β-unsaturated ketone moieties, which were also prepared starting from the macrocyclic lactones, produced macrocyclic lactams or ketones, respectively. The simple approach can be readily applied to the preparation of a variety of macrocyclic lactones, lactams, and ketones with tunable ring sizes.
Improved Method for the Synthesis of Palmitic Acid
Hostetler, Eric D.,Fallis, Stephen,McCarthy, Timothy J.,Welch, Michael J.,Katzenellenbogen, John A.
, p. 1348 - 1351 (1998)
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Synthesis of 23-, 25-, 27-, and 29-Membered (Z)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization
Iwasaki, Tomoya,Tajimi, Yuka,Kameda, Kenta,Kingwell, Callum,Wcislo, William,Osaka, Kazuyuki,Yamawaki, Mugen,Morita, Toshio,Yoshimi, Yasuharu
, p. 8019 - 8026 (2019/06/27)
A new strategy for the synthesis of 23-, 25-, 27-, and 29-membered (Z)-selective unsaturated and saturated macrocyclic lactones from commercially available 16- and 17-membered macrocyclic lactones and bromoalcohols by Wittig reaction, Yamaguchi macrolactonization, and photoinduced decarboxylative radical macrolactonization is described. The position of the unsaturated part in the macrocyclic lactones can be controlled by changing the number of carbons in the starting materials. This protocol can provide facile access to the desired large-ring (Z)-selective unsaturated and saturated macrocyclic lactones from simple starting materials.
Facile access to arsenic-containing triacylglycerides
Guttenberger, Nikolaus,Sagmeister, Peter,Glabonjat, Ronald A.,Hirner, Stefan,Francesconi, Kevin A.
supporting information, p. 362 - 364 (2017/01/03)
The previously unknown arsenic-containing triacylglycerides (AsTAGs) 3-((15-(dimethylarsinoyl)pentadecanoyl)oxy)propane-1,2-diyl dipalmitate 1 and 2-((15-(dimethylarsinoyl)pentadecanoyl)oxy)propane-1,3-diyl dipalmitate 2 have been synthesized. They will serve as model compounds in the search for naturally occurring AsTAGs, recently proposed natural constituents of fish oils.
Lipase-mediated regioselective modifications of macrolactonic sophorolipids
Sembayeva, Aliya,Berhane, Beniam,Carr, Jason A.
, p. 1873 - 1880 (2017/03/11)
Chemoenzymatic synthesis and modification of well-defined macrolactonic sophorolipid (SLML) analogues via a series of successive regioselective de-esterification/transesterification reactions is investigated. Of the lipases screened, Candida antartica lip
