143833-81-2Relevant articles and documents
One-pot oxidation/isomerization of Z-allylic alcohols with oxygen as stoichiometric oxidant
Koenning, Daniel,Hiller, Wolf,Christmann, Mathias
, p. 5258 - 5261 (2012)
A method for generating (E)-α,β-unsaturated aldehydes from Z-allylic alcohols or E/Z-mixtures is described. The one-pot procedure involves a Cu-catalyzed oxidation followed by an organocatalytic Z/E-isomerization with N,N-dimethylaminopyridine (DMAP).
Copper-free Sonogashira coupling of cyclopropyl iodides with terminal alkynes
De Carne-Carnavalet, Benoit,Archambeau, Alexis,Meyer, Christophe,Cossy, Janin,Folleas, Benoit,Brayer, Jean-Louis,Demoute, Jean-Pierre
, p. 956 - 959 (2011)
The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyclopropyl iodides, allowing an efficient access to a wide variety of functionalized alkynyl cyclopropanes.(Figure Presented)
Alkyne Aminopalladation/Heck and Suzuki Cascades: An Approach to Tetrasubstituted Enamines
Geffers, Finn J.,Jones, Peter G.,Kurth, Florens R.,Werz, Daniel B.
supporting information, p. 14846 - 14850 (2021/10/19)
Alkyne aminopalladation reactions starting from tosylamides are reported. The emerging vinylic Pd species are converted either in an intramolecular Heck reaction with olefinic units or in an intermolecular Suzuki reaction by using boronic acids exhibiting broad functional group tolerance. Tetra(hetero)substituted tosylated enamines are obtained in a simple one-pot process.
Fluorinated triazole-containing sphingosine analogues. Syntheses and in vitro evaluation as SPHK inhibitors
Escudero-Casao, Margarita,Cardona, Adrià,Beltrán-Debón, Raúl,Díaz, Yolanda,Matheu, M. Isabel,Castillón, Sergio
supporting information, p. 7230 - 7235 (2018/10/24)
Sphingosine analogues with a rigid triazole moiety in the aliphatic chain and systematic modifications in the polar head and different degrees of fluorination at the terminus of the alkylic chain were synthesized from a common alkynyl aziridine key synthon. This key synthon was obtained by enantioselective organocatalyzed aziridination and it was subsequently ring opened in a regioselective manner in acidic medium. Up to 16 sphingosine analogues were prepared in a straightforward manner. The in vitro activity of the obtained products as SPHK1 and SPHK2 inhibitors was evaluated, displaying comparable activity to that of DMS.
Sulfated tungstate as hydroxyl group activator for preparation of benzyl, including p-methoxybenzyl ethers of alcohols and phenols
Katkar, Kamlesh V.,Veer, Sachin D.,Akamanchi, Krishnacharya G.
supporting information, p. 1893 - 1901 (2016/11/25)
Sulfated tungstate was found to be an effective heterogeneous and reusable catalyst for hydroxy group activation–mediated preparation of benzylic ethers including p-methoxybenzylic ethers of a wide range of alcohols and phenols under mild reaction conditions.
Towards the total synthesis of marineosin A: Construction of the macrocyclic pyrrole and an advanced, functionalized spiroaminal model
Aldrich, Leslie N.,Berry, Cynthia B.,Bates, Brittney S.,Konkol, Leah C.,So, Miranda,Lindsley, Craig W.
supporting information, p. 4215 - 4218 (2013/07/26)
Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core of marineosin A in 5.1 % overall yield from (S)-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is subjected to Paal-Knorr pyrrole synthesis and ring-closing metathesis to afford the macrocycle. A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system through an acid-mediated hydroxy oxo amide cyclization strategy. Copyright
A very practical and selective method for PMB protection of alcohols
Chavan, Subhash P.,Harale, Kishor R.
experimental part, p. 4683 - 4686 (2012/09/05)
A very simple, practical and efficient one-step heterogeneous protocol for the PMB protection of alcohols using Amberlyst-15 has been developed. The stability and hazard issues regarding PMBCl and PMBBr are totally avoided by directly using anisyl alcohol for the protection. Alcohols are protected in very good yields. The selective mono-PMB protection of diols as well as di-PMB protection of diols was achieved in good yields, along with the demonstration of recyclability of the catalyst.
The first total synthesis of Topsentolide B3
Sreedhar, Eppakayala,Venkanna, Arramshetti,Chandramouli, Nagula,Babu, K. Suresh,Rao, Janaswamy Madhusudana
experimental part, p. 1078 - 1083 (2011/03/22)
The first total synthesis of the cytotoxic oxylipin Topsentolide B 3 has been accomplished in 15 steps with an overall yield of 24%. Starting with readily available cis-butene diol as a synthon, the synthesis involved Marouka allylation and Sha
Total synthesis of (+)-chloriolide
Haug, Timm T.,Kirsch, Stefan F.
supporting information; experimental part, p. 991 - 993 (2010/06/15)
The first total synthesis of (+)-chloriolide, a 12-membered macrolide from Chloridium virescens (var. chlamydosporum), was accomplished in a longest linear sequence of 20 steps from commercial materials in 7% overall yield. The Royal Society of Chemistry.
Allylic fluorination via an unusual alkene Z/E isomerisation
Laurenson, James A.B.,Meiries, Sebastien,Percy, Jonathan M.,Roig, Ricard
scheme or table, p. 3571 - 3573 (2009/12/01)
The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)-1-chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective substrate in Sharpless asymmetric dihydroxylation (AD) re
