65756-08-3Relevant academic research and scientific papers
A new approach to (+)-brefeldin A via a nickel-catalyzed coupling reaction of cyclopentenyl acetate and lithium 2-furylborate
Kobayashi, Yuichi,Watatani, Kengo,Kikori, Yuusuke,Mizojiri, Ryo
, p. 6125 - 6128 (1996)
Coupling reaction of 2 with 2-furylborate 14 in the presence of the nickel catalyst afforded 1,4-isomer 5 regio- and stereoselectively and the product 5 was applied to the synthesis of Bartlett's brefeldin intermediate 11.
Total Synthesis of trans-Resorcylide via Macrocyclic Stille Carbonylation
Luo, Yiyang,Yin, Xianglin,Dai, Mingji
, p. 482 - 485 (2019/02/19)
The resorcylic macrolides are important natural products with a wide range of remarkable biological activities. So far, most of the reported resorcylic macrolide syntheses use either macrolactonization or ring closing metathesis to build the corresponding macrocycle. In continuation of our efforts in developing novel carbonylation reactions to facilitate natural product total synthesis, we report herein a total synthesis of trans-resorcylide (1) featuring a palladium-catalyzed macrocyclic Stille carbonylation to build its 12-membered macrocycle.
Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling
Kang, Houng,Torruellas, Carilyn,Liu, Jinchu,Kozlowski, Marisa C.
, p. 5554 - 5558 (2018/09/29)
The first total synthesis of chaetoglobin A (1), which features a chiral axis between two identical highly oxygenated bicyclic cores, was successfully completed in 12 steps from 2,6-dimethoxytoluene. Vanadium-catalyzed oxidative phenol coupling, as a key
De Novo Asymmetric Synthesis of Phoracantholide J
Avocetien, Kenneth F.,Li, Jiazhen J.,Liu, Xiaofan,Wang, Yanping,Xing, Yalan,O'Doherty, George A.
, p. 4970 - 4973 (2016/10/14)
A de novo asymmetric total synthesis of the macrolide natural product (S)-phoracantholide J has been achieved in 10 steps from the commodity chemicals (1-pentyne, ethyl acrylate, acetaldehyde, and hydrogen). The asymmetry of the route was introduced by a Noyori reduction of a 3-yn-2-one, which makes the route equally amenable to the synthesis of either enantiomer. In addition, this route relies upon an alkyne zipper, a hydroalkynylation, and a macrolactonization to complete the synthesis.
Transition-metal-catalyzed synthesis of aspergillide B: An alkyne addition strategy
Trost, Barry M.,Bartlett, Mark J.
, p. 1322 - 1325 (2012/04/23)
A catalytic enantioselective formal total synthesis of aspergillide B is reported. This linchpin synthesis was enabled by the development of new conditions for Zn-ProPhenol catalyzed asymmetric alkyne addition. This reaction was used in conjunction with ruthenium-catalyzed trans-hydrosilylation to affect the rapid construction of a late-stage synthetic intermediate of aspergillide B to complete a formal synthesis of aspergillide B in a highly efficient manner.
Total synthesis of both enantiomers of macrocyclic lactone aspergillide C
Srihari,Sridhar
, p. 6690 - 6697 (2012/01/03)
A facile approach to the total synthesis of both enantiomers of the 14-membered macrolactone aspergillide C is described. The strategy employed was also utilized for the synthesis of C4-epimers of both the enantiomers of aspergillide C. The key reactions include Sharpless kinetic resolution, Achmatowicz reaction, Ferrier type alkynylation, hydrosilylation- protodesilylation, Corey-Bakshi-Shibata (CBS) mediated reduction, and Yamaguchi macrolactonization.
Total synthesis of (+)-brefeldin a
Wu, Yikang,Gao, Jian
supporting information; experimental part, p. 1533 - 1536 (2009/04/12)
(+)-Brefeldin A was synthesized through an efficient route, which features (1) construction of the five-membered ring from a Crimmins aldol via tandem Li-I exchange and carbanion-mediated cyclization with concurrent removal of the chiral auxiliary, (2) introduction of the lower side chain (C10 to C16) via a Rh-catalyzed Michael addition of a vinyl boronic acid, (3) stereoselective reduction of the C7 ketone with Sml2, and (4) a 2-methyl-6- nitrobenzoic anhydride-mediated (Shiina) lactonization.
Routine use of natural abundance deuterium NMR in a polypeptidic chiral oriented solvent for the determination of the enantiomeric composition of chiral building blocks.
Parenty, Arnaud,Campagne, Jean-Marc,Aroulanda, Christie,Lesot, Philippe
, p. 1663 - 1666 (2007/10/03)
[reaction: see text] Natural abundance deuterium 2D NMR spectroscopy in chiral liquid crystal was successfully used to efficiently analyze the enantiomeric composition of organic chiral building blocks involved in the syntheses of natural and synthetic bioactive products. The results reported here emphasize the high potential of this analytical strategy and prove its applicability for routinely determining enantiomeric excesses.
Catalytic enantioselective synthesis of macrolides via asymmetric alkylation
Jones, Graham B.,Huber, Robert S.,Chapman, Brant J.
, p. 1797 - 1809 (2007/10/03)
Catalytic enantioselective syntheses of the macrolides (R)-(-) phoracantholide and (R)-(+) lasiodiplodin have been achieved. Stereochemistry was introduced in using an arene chromium tricarbonyl derived catalyst, which mediated the enantioselective additi
New ligands for the titanium(IV)-induced asymmetric reduction of ketones with catecholborane
Almqvist,Torstensson,Gudmundsson,Frejd
, p. 376 - 377 (2007/10/03)
High to moderate enantiomeric excesses were achieved for the reduction of ketones with catecholborane in the presence of a titanium-based catalyst bearing the new optically active diols 1 a or 1 b as ligands. Of particular interest is the relatively high enantiomeric excess obtained in the reductions of linear nonaromatic methyl ketones.
