124356-91-8Relevant academic research and scientific papers
Synthesis and Biological Evaluation of Dichlorinated Chondramide Derivatives
Becker, Dominic,Kazmaier, Uli
, p. 4198 - 4213 (2015)
Straightforward synthetic protocols for the synthesis of new ethyl-substituted dichlorinated chondramides with different methyl-substitution patterns in the polyketide fragment have been developed. The methyl groups at the ?-position can be removed comple
10. The enantioselective synthesis of the 'Southern Part' of soraphen A
Loubinoux,Sinnes,O'Sullivan,Winkler
, p. 122 - 128 (1995)
Using a series of enantioselective aldol condensations followed by an ester enolate addition, the cyclic hemiacetal 2 was prepared stereospecifically. Hemiacetal 2 represents the synthetically most challenging 'southern part' of the antifungal macrolide s
Divergent mechanistic routes for the formation of gem-dimethyl groups in the biosynthesis of complex polyketides
Poust, Sean,Phelan, Ryan M.,Deng, Kai,Katz, Leonard,Petzold, Christopher J.,Keasling, Jay D.
, p. 2370 - 2373 (2015)
The gem-dimethyl groups in polyketide-derived natural products add steric bulk, accordingly, lend increased stability to medicinal compounds, however, our ability to rationally incorporate this functional group in modified natural products is limited. In
The vinylogous aldol reaction of N-Sulfinyl metallodienamines
Yu, Po-Cheng,Chatare, Vijay K.,Patel, Harsh,DeBrosse, Charles,Andrade, Rodrigo B.
supporting information, (2020/01/08)
The discovery and development of the vinylogous aldol reaction of N-sulfinyl metallodienamines with aldehydes and ketones is described. The diastereoselectivity of the reaction, first reported in 2017 as a key step in the total asymmetric synthesis of (?)-albocycline, has been corrected by Mosher ester analysis. The reaction has been optimized and the scope investigated, with yields ranging from 68–89% and diastereomeric ratios as high as 5.9:1. Extensive investigation into the mechanisms affecting stereoselectivity revealed that two stereochemical erosion pathways are operative when using LiHMDS and SnCl4. A transition state supported by DFT calculations has been advanced to rationalize the stereochemical course of the reaction.
Racemization of α-Alkyl-β-Keto Esters and Enantioselective Total Synthesis of Two C-2′′′Epimers of Plant Glycerolipid Santinol C
Wu, Wen-Ju,Li, Mei-Mei,Liu, Bo,Wu, Yikang
supporting information, p. 3169 - 3173 (2019/05/21)
It is broadly believed that optically active α-alkyl-β-keto esters racemize very quickly. Nevertheless, no one really knows how fast the racemization is. In fact, such species are hardly attainable to date. Now, a facile entry to these greatly understudied esters has been found and their racemization has been studied for the first time. The results showed that under neutral or slightly acidic conditions such species were much more stable than one might expect, though they did racemize rapidly under basic conditions. In light of the new findings, santinol C was also synthesized in enantiopure forms.
Biomimetic Synthesis of Lankacidin Antibiotics
Zheng, Kuan,Shen, Defeng,Hong, Ran
supporting information, p. 12939 - 12942 (2017/09/26)
We devised short syntheses of lankacidinol and lankacyclinol that feature biomimetic Mannich macrocyclization. The modular construction of the carbon framework of these compounds is amenable to rapid structural diversification for the development of antib
Concise synthesis and revision of the proposed biogenesis of helicascolides
Zheng, Kuan,Xie, Changmin,Hong, Ran
, p. 4459 - 4464 (2017/10/30)
A concise synthesis of helicascolides A, B and C was achieved in three to five steps from commercially available materials. The key transformations of the synthesis include an Evans-Metternich anti-aldol reaction of the known β-keto imide 10 and strategic
Substrate structure-activity relationships guide rational engineering of modular polyketide synthase ketoreductases
Bailey, Constance B.,Pasman, Marjolein E.,Keatinge-Clay, Adrian T.
supporting information, p. 792 - 795 (2016/01/12)
Modular polyketide synthase ketoreductases can set two chiral centers through a single reduction. To probe the basis of stereocontrol, a structure-activity relationship study was performed with three α-methyl, β-ketothioester substrates and four ketoreductases. Since interactions with the β-ketoacyl moiety were found to be most critical, residues implicated in contacting this moiety were mutated. Two mutations were sufficient to completely reverse the stereoselectivity of the model ketoreductase EryKR1, converting it from an enzyme that generates (2S,3R)-products into one that yields (2S,3S)-products.
Formal total synthesis of kendomycin by way of alkyne metathesis/gold catalysis
Hoffmeister, Laura,Persich, Peter,Fuerstner, Alois
supporting information, p. 4396 - 4402 (2014/05/06)
In an attempt to study the ability of the latest generation of alkyne metathesis catalysts to process sterically hindered substrates, two different routes to the bacterial metabolite kendomycin (1) were explored. Whereas the cyclization of the overcrowded
Synthesis, molecular editing, and biological assessment of the potent cytotoxin leiodermatolide
Mailhol, Damien,Willwacher, Jens,Kausch-Busies, Nina,Rubitski, Elizabeth E.,Sobol, Zhanna,Schuler, Maik,Lam, My-Hanh,Musto, Sylvia,Loganzo, Frank,Maderna, Andreas,Fürstner, Alois
supporting information, p. 15719 - 15729 (2014/12/11)
It was by way of total synthesis that the issues concerning the stereostructure of leiodermatolide (1) have recently been solved; with the target now being unambiguously defined, the mission of synthesis changes as to secure a meaningful supply of this ex
