454482-62-3Relevant academic research and scientific papers
Synthetic studies on pseudolaric acid B: Enantioselective synthesis of C4,C10-di-epi-trans-fused [5-7]-bicyclic skeleton
Guo, Rui,Zhai, Hongbin,Li, Yun
supporting information, p. 1400 - 1402 (2020/10/07)
Studies on the synthesis of antifungal and anticancer natural product, pseudolaric acid B, have led to the enantioselective synthesis of di-epi-trans-fused [5–7]-bicyclic core skeleton. The synthesis was achieved in 10 linear steps, which features the Sharpless asymmetric epoxidation, cyanide-opening reaction of epoxide, and intramolecular [5 + 2] cycloaddition reaction as the key transformations. The stereochemistry was determined by the X-ray crystallographic analysis.
A concise total synthesis of puberulic acid, a potent antimalarial agent
Sennari, Goh,Hirose, Tomoyasu,Iwatsuki, Masato,Omura, Satoshi,Sunazuka, Toshiaki
supporting information, p. 8715 - 8718 (2014/07/22)
Efficient and practical total synthesis of puberulic acid has been accomplished via 8 steps, with 54% overall yield, and only two C-C bond formations, without the introduction of oxygen atoms into the core skeleton. Construction of the tropolone framework as the key transformation was achieved by multi-tandem oxidation of the aliphatic-triol, from d-(+)-galactose as the starting material.
2-(Selenocyanatomethyl)-2-propenol-A convenient synthon for ligation via the deselenative allylic rearrangement of allyl selenosulfides: Preparation, functional group compatibility, and application
Lachkar, David,Boudet, Caroline,Guinchard, Xavier,Crich, David
, p. 944 - 953 (2013/02/22)
The preparation and reactions of 2-(selenocyanatomethyl)-2-propenol are described and reveal the compatibility of the allylic selenocyanate group with a range of mild oxidizing and Lewis acidic conditions. 2-(Selenocyanatomethyl)-2- propenol and its derivatives are employed in the functionalization of simple and amino acid derived thiols in methanolic solution at room temperature to give 2-(hydroxymethyl)allyl sulfides in good to excellent yield.
Exploratory studies toward the synthesis of the peroxylactone unit of plakortolides
Barnych, Bogdan,Vatèle, Jean-Michel
scheme or table, p. 3717 - 3724 (2012/06/30)
Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of β-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the ep
Inhibition of Hsp90 with resorcylic acid macrolactones: Synthesis and binding studies
Day, James E. H.,Sharp, Swee Y.,Rowlands, Martin G.,Aherne, Wynne,Lewis, William,Mark Roe,Prodromou, Chrisostomos,Pearl, Laurence H.,Workman, Paul,Moody, Christopher J.
scheme or table, p. 10366 - 10372 (2010/12/29)
A series of resorcylic acid macrolactones, analogues of the natural product radicicol has been prepared by chemical synthesis, and evaluated as inhibitors of heat shock protein 90 (Hsp90), an emerging attractive target for novel cancer therapeutic agents.
Total synthesis of pseudolaric acid A
Geng, Zhe,Chen, Bin,Chiu, Pauline
, p. 6197 - 6201 (2007/10/03)
(Chemical Equation Presented) The antiangiogenic and cytotoxic natural product pseudolaric acid A ((-)-1) has been obtained by a 26-step synthetic route. This enantioselective synthesis employed an intramolecular carbene cyclization cycloaddition cascade
A new synthetic approach to 5-dethia-4-methyl-5-oxacephems
Ka?uza, Zbigniew,Kazimierski, Arkadiusz,Lewandowski, Krzysztof,Suwińska, Kinga,Szcz?sna, Beata,Chmielewski, Marek
, p. 5893 - 5903 (2007/10/03)
Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized.
Toward a total synthesis of okilactomycin. 2. A metathesis-based approach to the heavily functionalized cyclohexane ring
Boulet, Serge L.,Paquette, Leo A.
, p. 895 - 900 (2007/10/03)
An attempt to access in an enantioselective fashion, a highly substituted cyclohexane as required for the northeastern sector of okilactomycin is described. The application of Oppolzer's sultam chemistry, involving in particular an optically and chemicall
Tandem radical cyclisations: Synthesis of lysergic acid derivatives
Ozlu,Cladingboel,Parsons
, p. 2183 - 2206 (2007/10/02)
A novel free radical cyclisation approach for the synthesis of lysergic acid analogues has been investigated. The homolytic cleavage of carbon- bromine bond, mediated by tri-n-butyltin hydride, led to the development of a method for the construction of 3,
