271797-09-2Relevant academic research and scientific papers
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
, p. 15593 - 15598 (2021/10/12)
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
Asymmetric Synthesis of Saturated Hydroxy Fatty Acids and Fatty Acid Esters of Hydroxy Fatty Acids
Mountanea, Olga G.,Limnios, Dimitris,Kokotou, Maroula G.,Bourboula, Asimina,Kokotos, George
, p. 2010 - 2019 (2019/03/07)
The recent discovery of a novel class of endogenous lipids, named Fatty Acid esters of Hydroxy Fatty Acids (FAHFAs), that present antidiabetic and anti-inflammatory activities, has attracted the interest on hydroxy fatty acids (HFAs) and their derivatives
Stereoselective synthesis of dendrodolide-L
Bujaranipalli, Sheshurao,Das, Saibal
, p. 254 - 260 (2017/03/01)
An efficient stereoselective total synthesis of 12-membered macrolide dendrodolide L has been achieved. The key reactions involved are Keck asymmetric allylation, Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu reaction and ring-closing metathesis reaction.
Titanium cis-1,2-diaminocyclohexane (cis-DACH) salalen catalysts for the asymmetric epoxidation of terminal non-conjugated olefins with hydrogen peroxide
Wang, Qifang,Neud?rfl, J?rg-M.,Berkessel, Albrecht
, p. 247 - 254 (2015/07/07)
Chiral Ti salalen complexes catalyze the asymmetric epoxidation of terminal non-conjugated olefins with hydrogen peroxide. Modular ligands based on cis-1,2-diaminocyclohexane (cis-DACH) were developed, giving high yields and enantiomeric excesses (ee, up to 96%) at catalyst loadings as low as 0.1-0.5mol%, and even under solvent-free conditions.
Titanium salalen catalysts based on cis-1,2-diaminocyclohexane: Enantioselective epoxidation of terminal non-conjugated olefins with H 2O2
Berkessel, Albrecht,Guenther, Thomas,Wang, Qifang,Neudoerfl, Joerg-M.
supporting information, p. 8467 - 8471 (2013/09/02)
Terminal, non-conjugated olefins, such as 1-octene, are difficult to epoxidize asymmetrically. Ti salalen complexes based on cis-1,2- diaminocyclohexane catalyze this demanding reaction giving high yields and enantioselectivities (up to 95 % ee), with H2O2 as the oxidant. The X-ray structures of the μ-oxo and peroxo complexes shed light on the coordination behavior of this novel class of ligands.
Stereoselective total synthesis of (-)-pyrenophorol
Yadav,Subba Reddy,Subba Reddy
scheme or table, p. 5984 - 5986 (2010/02/28)
An efficient stereoselective total synthesis of (-)-pyrenophorol 1 is described. The key steps involved in this synthesis are hydrolytic kinetic resolution (HKR), MacMillan α-hydroxylation, Horner-Wadsworth-Emmons (HWE) reaction, and Mitsunobu cyclization
Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
Sabitha, Gowravaram,Gopal, Peddabuddi,Yadav, Jhillu S.
scheme or table, p. 1493 - 1499 (2009/12/01)
The total synthesis of lactone 1 has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions.
