74726-77-5Relevant academic research and scientific papers
Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G
Jung, Youngeun,Singh, Dileep Kumar,Kim, Ikyon
, p. 2689 - 2693 (2016)
The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and S
Reinvestigating the acyl cyclization to the precursor of diptoindonesin G
Li, Nan-Sheng,Greene, Geoffrey L.
, (2021/03/29)
We reinvestigated the synthesis of the precursor of diptoindonesin G (2) by the intramolecular acyl cyclization of compound 1 or compound 3 in the presence of trifluoroacetic anhydride (TFAA) [1,2]. Although the reaction of 3 with TFAA generated 2 smoothl
Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum
Murata, Chihiro,Ogura, Tetsuhiro,Narita, Shuhei,Kondo, Anna P.,Iwasaki, Natsumi,Saito, Tamao,Usuki, Toyonobu
, p. 1428 - 1433 (2016/02/19)
4-Methyl-5-pentylbenzene-1,3-diol (MPBD) is a secondary metabolite of SteelyA polyketide synthase, which controls cell aggregation and spore maturation of Dictyostelium discoideum. In this study, chemical synthesis of MPBD and its derivatives was achieved. Structure-activity relationship (SAR) studies for antimicrobial activities against Escherichia coli and Bacillus subtilis were also conducted.
Three-component coupling approach toward the synthesis of a resorcylic acid lactone framework
Sugiyama, Sakae,Fuse, Shinichiro,Takahashi, Takashi
experimental part, p. 6654 - 6658 (2011/09/20)
A resorcylic acid lactone (RAL) framework was constructed based on a three-component coupling approach. The key step was the intermolecular alkylation of a protected cyanohydrin with an aromatic scaffold, and the subsequent carbonylative esterification of the aryl iodide with an alcohol. This sequence allowed the rapid assembly of three components without extra protection/deprotection steps. This synthetic strategy enables the ketone at the 2′ position to be masked as a protected cyanohydrin during the ester formation, thus avoiding an undesired isocoumarin formation. This method should be widely applicable to the synthesis of various types of RAL frameworks.
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.
Synthesis of phosphonate 3-phthalidyl esters as prodrugs for potential intracellular delivery of phosphonates
Dang, Qun,Brown, Brian S.,Van Poelje, Paul D.,Colby, Timothy J.,Erion, Mark D.
, p. 1505 - 1510 (2007/10/03)
A new prodrug approach for intracellular delivery of phosphonates was developed via the synthesis of 3-phthalidyl esters of 1- naphthalenemethylphosphonate. This approach is advantageous over the traditional acyloxymethyl phosphonate prodrugs, because the
Total synthesis of vancomycin - Part 1: Design and development of methodology
Nicolaou,Li, Hui,Boddy, Christopher N. C.,Ramanjulu, Joshi M.,Yue, Tai-Yuen,Natarajan, Swaminathan,Chu, Xin-Jie,Braese, Stefan,Ruebsam, Frank
, p. 2584 - 2601 (2007/10/03)
o-Halosubstituted aromatic triazenes (e.g. I, Scheme 1) react with aryloxides (e.g. II, Scheme 1) in the presence of CuBr · Me2S, K2CO3 and pyridine in acetonitrile at reflux to afford biaryl ethers (e.g. V, Scheme 1). This general methodology (Tables 1 and 2) was applied to the construction of the C-O-D and D-O-E vancomycin model systems 37 (Scheme 2) and 50 (Scheme 3), demonstrating its potential in a projected total synthesis of vancomycin (1. Figure 1). For the construction of the vancomycin model AB biaryl ring system, a sequential strategy involving a Suzuki coupling of the C-O-D aryl iodide 74 (Scheme 7) and boronic acid 53 (Scheme 4), followed by macrolactamization was demonstrated, in which the preformed C-O-D ring framework served to preorganize the precursor for cyclization. The latter investigation led to Suzuki-coupling-based asymmetric synthesis of biaryl systems in which 2,2-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) was found to be the optimum ligand (Tables 3 and 4).
A Suzuki coupling-macrolactamization approach to the AB-COD bicyclic system of vancomycin
Nicolaou,Ramanjulu,Ramanjulu, Joshi M.,Natarajan,Natarajan, Swaminathan,Brase,Braese, Stefan,Li,Li, Hui,Boddy,Boddy, Christopher N. C.,Rubsam,Ruebsam, Frank
, p. 1899 - 1900 (2007/10/03)
The effectiveness of the Suzuki coupling reaction in the formation of the AB biaryl moiety and the beneficial role of a preexisting COD ring system in a lactamization approach to the AB-COD ring system of vancomycin is demonstrated.
Taxane synthesis through intramolecular pinacol coupling at C-1 - C-2. Highly oxygenated C-aromatic taxanes
Swindell, Charles S.,Fan, Weiming
, p. 1109 - 1118 (2007/10/03)
Chiral, nonracemic intramolecular pinacol coupling substrates 3/20 and 30 have been prepared from ethyl isopropyl ketone and acryloyl chloride, which provide the A-ring and either o-iodobenzyl alcohol or 2,4-dimethoxybenzyl alcohol, which provide the respective aromatic C-rings, in 14-16 linear steps in overall yields of approximately 20%. Potential pinacol coupling substrate 23 could not be made available for investigation due to intervening pinacol rearrangement in the acetonide formation step. 3/20 undergo stereoselective cyclizations mediated by TiCl4-Zn in which the C-9 oxygen substituent plays the dominant role in determining the stereochemical outcome at C-1 and C-2 in the respective tricyclic products 4 and 21. The formation of 21 is the more stereoselective process. The reagent of choice for the transformation of 30 into 31 is SmI2, which, although less stereoselective than TiCl4-Zn, leads to higher yielding carbon-carbon bond formation relative to carbonyl reduction. These pinacol cyclizations are interpreted to occur through endo boat-chair transition structures that prefer to orient the developing C-2 substituent and the preexisting C-9 substituent equatorially. Pinacol product 31 was converted through three additional steps into 40 having a B-ring closely related to that of taxol. We believe that these studies indicate pinacol cyclizations at C-1-C-2 to have considerable potential for producing advanced intermediates for syntheses of taxol and related complex taxanes.
Naturally Occuring Dibenzofurans. Part 9. A Convenient Synthesis of Phthalides: The Synthesis of Methyl Di-O-methylporphyrilate
Sargent, Melvyn V.
, p. 231 - 236 (2007/10/02)
A convenient synthesis of phthalides from o-halogenobenzyl alcohols is described.This method is then applied to the synthesis of methyl di-O-methylporphyrilate (methyl 1,3-dihydro-4,10-dimethoxy-8-methyl-3-oxoisobenzofuro
