347886-00-4Relevant articles and documents
Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter
Dong, Kaiwu,Li, Huimin,Ren, Xinyi,Shen, Chaoren,Tang, Lin,Wang, Peng
supporting information, p. 3561 - 3566 (2021/05/29)
A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.
Synthesis of 3-deoxy-2-uloses via the indium-mediated allylation reaction
Gintner, Manuel,Denner, Christian,Schm?lzer, Christoph,Fischer, Michael,Frühauf, Peter,K?hlig, Hanspeter,Schmid, Walther
, (2019/05/15)
Abstract: We utilized the indium-mediated allylation reaction for the synthesis of carbohydrate structures containing the 3-deoxy-2-ulose motif, a barely investigated compound class. The stereoselective outcome can be controlled by the presence or absence of a chelating group in α-position to the carbonyl function. By introduction of an UV-active allyl building block, we enabled epimer separation by HPLC towards the synthesis of 3-deoxy-d-glycero-d-galacto-2-nonulose, the carboxyl-reduced analogue of widely distributed 3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn). Ozonolysis of the introduced 2-C-methylidenepropan-1-ol motif provided the desired 3-deoxy-2-uloses. Graphical abstract: [Figure not available: see fulltext.].
Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents
Alazet, Sébastien,Le Vaillant, Franck,Nicolai, Stefano,Courant, Thibaut,Waser, Jerome
supporting information, p. 9501 - 9504 (2017/07/22)
A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.
Convergent stereoselective and efficient synthesis of furanic-steroid derivatives
Farhane, Siham,Fournier, Michelle-Audrey,Maltais, René,Poirier, Donald
experimental part, p. 2434 - 2440 (2011/05/04)
The stereoselective synthesis of furanic-steroid derivatives involving ring-closing metathesis and catalytic hydrogenation as key steps is described. The synthetic strategy was first illustrated by the synthesis of the furanic-estrane derivative 1 in seven steps starting from estrone and 2-methylene-propane-1,3-diol. This compound initially targeted as a potential inhibitor of 17β-hydroxysteroid dehydrogenase type 1 by a docking experiment was found to inhibit the enzyme. The scope of this new strategy was also extended to furanic-androstane derivatives by synthesizing compound 20.
Synthetic studies toward pectenotoxin 2. Part I. Stereocontrolled access to the C10-C22 fragment
Aho, Jatta E.,Salomaeki, Elina,Rissanen, Kari,Pihko, Petri M.
supporting information; experimental part, p. 4179 - 4182 (2009/05/27)
(Chemical Equation Presented) A highly stereocontrolled and efficient synthesis for a fully functionalized C10-C22 fragment of pectenotoxin 2 Is described using a convergent sequence involving a stereoselective methylation of β-hydroxyketone as a key step.
Transformation of esters into 2-substituted allyl halides via tertiary cyclopropanols: Application in the stereoselective synthesis of (2S,3S,7S)-3,7-dimethyl-2-pentadecyl acetate, the sex pheromone of the pine sawfly Neodiprion sertifer
Bekish, Andrei V.,Prokhorevich, Konstantin N.,Kulinkovich, Oleg G.
, p. 5069 - 5075 (2007/10/03)
(2S,3S,7S)-3,7-Dimethyl-2-pentadecyl acetate (ac-1), the sex pheromone of the pine sawfly Neodiprion sertifer, has been newly synthesized by the transformation of the corresponding esters 8 and 12 into 2-oxyalkyl-substituted allyl bromides 4 and 5 via ter
A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids
Chen, Bin,Ko, Rebecca Y. Y.,Yuen, Mabel S. M.,Cheng, Kin-Fai,Chiu, Pauline
, p. 4195 - 4205 (2007/10/03)
An approach toward the synthesis of the antifungal and cytotoxic pseudolaric acids based on the tandem metal carbene cyclization-cycloaddition reaction is described. Using this strategy, the advanced intermediate 3a bearing three of the four stereocenters
A rhodium carbene cyclization-cycloaddition cascade strategy toward the pseudolaric acids.
Chiu,Chen,Cheng
, p. 1721 - 1724 (2007/10/03)
A rhodium carbene intramolecular cyclization-cycloaddition cascade was employed as the key reaction in the synthesis of the nucleus of the cytotoxic diterpenoids pseudolaric acids A and B.
Propanol derivatives
-
, (2008/06/13)
Propanol derivatives of formula (I) wherein X is a leaving group; R1 is H or a protecting group; and R2 is H, and R3 is a group--CH2 Y wherein Y is a leaving group; or R2 and R3 together form =CH2. The propanol derivatives of the formula (I) are useful as multifunctional alkylating agents.
