106356-53-0Relevant articles and documents
Stereoselective synthesis of the C1-C12 fragment of the cytotoxic macrolide FD-891
Murga, Juan,García-Fortanet, Jorge,Carda, Miguel,Marco, J. Alberto
, p. 2830 - 2832 (2004)
A stereoselective synthesis of the C1-C12 fragment of the naturally occurring, cytotoxic macrolide FD-891, is described. The initial chirality was created via an asymmetric Evans aldol reaction. Two other asymmetric reactions, a Sharpless epoxidation and
Stereoselective synthesis of (-)-galantinic acid
Dubey, Abhishek,Harbindu, Anand,Kumar, Pradeep
, p. 901 - 904 (2011)
An efficient and highly concise synthesis of (-)-galantinic acid has been achieved using an asymmetric allylation reaction of Garner's aldehyde. Georg Thieme Verlag Stuttgart - New York.
Total Synthesis and Tentative Structural Elucidation of Cryptomoscatone E3: Interplay of Experimental and Computational Studies
Novaes, Luiz F.T.,Sarotti, Ariel M.,Pilli, Ronaldo A.
, p. 12027 - 12037 (2015)
A successful combination of computational chemistry and total synthesis was explored to tentatively elucidate the absolute configuration of cryptomoscatone E3, a polyketide isolated from the Brazilian tree Cryptocarya mandiocanna. Two independent synthetic approaches are discussed based on asymmetric allylation, ring closing metathesis, and aldol reactions.
Enantioselective Total Synthesis of Diocollettines A
Kawamoto, Yuichiro,Kobayashi, Toyoharu,Ito, Hisanaka
supporting information, p. 5813 - 5816 (2019/07/08)
The first enantioselective total synthesis of diocollettines A was accomplished in only six steps from a known compound. A short and practical synthetic route was disclosed, featuring an intensive investigation of the stereoselective aldol reaction as a key step using an easily prepared aldehyde moiety and an enone derivative. The synthetic scheme also includes the efficient stereocontrolled construction of the tricyclic skeleton of diocollettines A by intramolecular acetal formation, stereoselective dihydroxylation, and intramolecular ether cyclization.
Total synthesis and configurational assignment of the marine natural product haliclamide
Pfeiffer, Bernhard,Speck-Gisler, Sandra,Barandun, Luzi,Senft, Ursula,De Groot, Claire,Lehmann, Irene,Ganci, Walter,Gertsch, Juerg,Altmann, Karl-Heinz
, p. 2553 - 2563 (2013/05/22)
The marine natural product haliclamide has been synthesized based on macrocyclization by ring-closing olefin metathesis. Using either enantiomer of two of the four building blocks that were employed to assemble the diene precursor for the metathesis reaction, three non-natural isomers of haliclamide were also prepared. On the basis of the comparison of the 1H and 13C NMR spectra of the individual stereoisomers with literature data for the natural product, the configuration of the previously unassigned stereocenters at C9 and C20 of haliclamide could be determined to be S for both carbons. The absolute configuration of haliclamide thus is 2S, 9S, 14R, 20S. The antiproliferative activity of synthetic haliclamide against several human cancer cell lines was found to be in the high μM range. The compound showed no antifungal or antibiotic activity.