699-13-8Relevant articles and documents
Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols
Hamel, Jean-Denys,Paquin, Jean-Fran?ois
, p. 11 - 23 (2018/10/20)
The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclizatio
Total synthesis of AMF-26, an antitumor agent for inhibition of the golgi system, targeting adp-ribosylation factor 1
Shiina, Isamu,Umezaki, Yuma,Ohashi, Yoshimi,Yamazaki, Yuta,Dan, Shingo,Yamori, Takao
supporting information, p. 150 - 159 (2013/02/23)
An effective method for the total synthesis of 1 (AMF-26), a potentially promising new anticancer drug that disrupts the Golgi system by inhibiting the ADP-ribosylation factor 1 (Arf1) activation, has been developed for the first time. The construction of
O -substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: The utility of methylthiomethyl ethers
Parsons, Scott R.,Hooper, Joel F.,Willis, Michael C.
, p. 998 - 1000 (2011/05/15)
Combining α-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]ClO4 results in efficient intermolecular alkyne hydroacylation to deliver α-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.(Figure Presented)
Total synthesis of (+)-papulacandin D
Denmark, Scott E.,Kobayashi, Tetsuya,Regens, Christopher S.
supporting information; experimental part, p. 4745 - 4759 (2010/08/06)
A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria.
Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin
Andrey, Olivier,Vidonne, Annick,Alexakis, Alexandre
, p. 7901 - 7904 (2007/10/03)
The asymmetric Michael addition of propionaldehyde to (2E)-(3-nitro-but-2-enyloxymethyl)-benzene 8, catalyzed by the chiral diamine (S,S)-N-iPr-2,2′-bipyrrolidine, afforded, with 93% ee, a precursor 9 of (-)-botryodiplodin. The nitro functionality of 9 was converted to a ketone via a Nef reaction to give, after a few steps, the enantiomerically enriched (-)-botryodiplodin.
Significant acceleration of 6π-azaelectrocyclization resulting from a remarkable substituent effect and formal synthesis of the ocular age pigment A2-E by a new method for substituted pyridine synthesis
Tanaka,Mori,Yamamoto,Katsumura
, p. 3099 - 3110 (2007/10/03)
The remarkable acceleration of 6π-azaelectrocyclization due to the combination of the C4-carbonyl and the C6-alkenyl or phenyl substituents in 1-azatrienes was found. This observation was rationalized by considering the remarkable orbital interaction between the HOMO and LUMO of 1-azatrienes, which were obtained by molecular orbital calculations. The formal synthesis of the unusual retinal metabolite, A2-E, was achieved by two types of the new one-pot synthesis of substituted pyridines by utilizing the obtained facile 6π-azaelectrocyclization, one of which is compatible with the proposed metabolic pathway of A2-E.
Polythiophene anti-tumor agents
-
, (2008/06/13)
Novel polythiophene compounds useful as anti-tumor agents are described. Preferred compounds of the formula: STR1 wherein n is 0-2 and R2 and R3 are optionally substituted 2-thienyl or 3-thienyl have been found to exhibit selective c
Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system
Nicolaou,Liu,Yang,Ueno,Sorensen,Claiborne,Guy,Hwang,Nakada,Nantermet
, p. 634 - 644 (2007/10/02)
A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.
