32863-01-7Relevant academic research and scientific papers
Development of an efficient route toward meiogynin A-inspired dual inhibitors of Bcl-xL and Mcl-1 anti-apoptotic proteins
Desrat, Sandy,Remeur, Camille,Roussi, Fanny
, p. 5520 - 5531 (2015/05/20)
The synthesis, on a large scale, with very good yield and er via an efficient strategy, of a chiral 4-substituted 2-cyclohexenone intermediate, was a milestone in the synthesis of seven analogues of meiogynin A, a natural sesquiterpenoid dimer. These comp
From meiogynin A to the synthesis of dual inhibitors of Bcl-xL and Mcl-1 anti-apoptotic proteins
Desrat,Remeur,Gény,Rivière,Colas,Dumontet,Birlirakis,Iorga,Roussi
, p. 8593 - 8596 (2014/07/22)
The synthesis of one of the most potent dual inhibitors of the anti-apoptotic proteins Bcl-xL and Mcl-1 is reported. This analogue of a natural sesquiterpenoid dimer meiogynin A was elaborated by a convergent asymmetric synthesis with 36% yield in ten steps. the Partner Organisations 2014.
Methodology for in situ protection of aldehydes and ketones using trimethylsilyl trifluoromethanesulfonate and phosphines: Selective alkylation and reduction of ketones, esters, amides, and nitriles
Yahata, Kenzo,Minami, Masaki,Yoshikawa, Yuki,Watanabe, Kei,Fujioka, Hiromichi
, p. 1298 - 1307 (2014/01/06)
A methodology for selective transformations of ketones, esters, Weinreb amides, and nitriles in the presence of aldehydes has been developed. The use of a combination of PPh3-trimethylsilyl trifluoromethanesulfonate (TMSOTf) promotes selective transformation of aldehydes to their corresponding, temporarily protected, O,P-acetal type phosphonium salts. Because, hydrolytic work-up following ensuing reactions of other carbonyl moieties in the substrates liberates the aldehyde moiety, a sequence involving aldehyde protection, transformation of other carbonyl groups, and deprotection can be accomplished in a one-pot manner. Furthermore, the use of PEt3 instead of PPh 3 enables ketones to be converted in situ to their corresponding O,P-ketal type phosphonium salts and, consequently, selective transformations of esters, Weinreb amides, and nitriles in the presence of ketones can be performed. This methodology is applicable to various dicarbonyl compounds, including substrates that possess heteroaromatic skeletons and hydroxyl protecting groups.
Reversing the reactivity of carbonyl functions with phosphonium salts: Enantioselective total synthesis of (+)-centrolobine
Fujioka, Hiromichi,Yahata, Kenzo,Kubo, Ozora,Sawama, Yoshinari,Hamada, Tomohito,Maegawa, Tomohiro
supporting information; experimental part, p. 12232 - 12235 (2012/01/30)
Step saver: Carbonyl groups with lower reactivities can be transformed in the presence of more reactive ones by treatment with PPh3 (or PEt3) and TMSOTf prior to the reaction (see scheme; TMS=trimethylsilyl, Tf=trifluoromethanesulfonyl). This methodology can be applied to reduction and alkylation reactions, and enabled the short asymmetric total synthesis of (+)-centrolobine with the highest overall yield reported to date.
Chemoenzymatic preparation of functionalized bicyclo[3.2.1]octenone and practical utilization
Ito, Shinichiro,Tosaka, Ayako,Hanada, Keisuke,Shibuya, Masatoshi,Ogasawara, Kunio,Iwabuchi, Yoshiharu
, p. 176 - 185 (2008/09/19)
A practical route for the synthesis of both enantiomers of a functionalized bicyclo[3.2.1]octenone, which is potentially useful as a versatile chiral building block, has been developed from 1,4-cyclohexanedione monoethylene acetal by employing proline-cat
NEW CARBONYLATED (AZA)CYCLOHEXANES AS DOPAMINE D3 RECEPTOR LIGANDS
-
, (2008/06/13)
The invention relates to compounds of the general formula (I): to the process for preparing them, and to the use thereof as a therapeutic agent.
Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization
Itagaki, Noriaki,Kimura, Mari,Sugahara, Tsutomu,Iwabuchi, Yoshiharu
, p. 4185 - 4188 (2007/10/03)
(Chemical Equation Presented) The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and encto-7-hydroxybicyclo[3.2.1]octan- 2-one, featuring an α-amino acid catalyzed intramolecular aldolization of σ-symmetric substrates, are des
NEW DERIVATIVES OF PYRIDIL PIPERAZINE OR PYRIDAZINYL PIPERAZYL, PROCESS FOR PRODUCTION THEREOF AND MEDICAMENTS CONTAINING THESE COMPOUNDS
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, (2008/06/13)
Compounds of formula I in which R1 denotes hydrogen, lower alkyl, lower alkenyl, cycloalkyl, cycloalkenyl, an optionally substituted monocyclic or bicyclic aryl, an optionally substituted hetaryl, an optionally substituted arylalkyl or one of the groups —OR2, —NR3R4, W denotes nitrogen or X, Z independently of one another denote nitrogen or CH and in the case that W denotes a nitrogen atom, X must be the group, A denotes a valency dash or a carbonyl group, B denotes a valency dash or a C1-C6 alkylene chain optionally substituted once or several times by lower alkyl or an OR2 group, D denotes a valency dash and, in the case that X is a nitrogen atom, can also be a carbonyl group in which case A, B and D may not simultaneously denote a valency dash, R2 denotes hydrogen, lower alkyl or arylalkyl, R3 and R4 independently of one another denote hydrogen or lower alkyl or together with the nitrogen atom to which they are bound form a five to six-membered heterocyclic ring, R5 denotes hydrogen or a group OR2, processes for the production thereof as well as pharmaceutical agents containing these compounds for the treatment of diseases which are the result of thrombo-embolic events.
Stemodin synthesis (II) - Highly diastereoselective formal total synthesis of - -stemodin via Pd2+ promoted cycloalkenylation reaction
Toyota, Masahiro,Seishi, Takashi,Fukumoto, Keiichiro
, p. 3673 - 3686 (2007/10/02)
Diastereoface-selective Pd2+-promoted cycloalkenylation reaction (22→24) has been employed as the key step for a conceptually new and highly diastereocontrolled formal total synthesis of - -stemodin (1). Interestingly, the synthetic intermediat
Pd2+-promoted cyclization in tetracyclic diterpene synthesis highly diastereoselective formal total synthesis of (±)-stemodin
Toyota, Masahiro,Seishi, Takashi,Fukumoto, Keiichiro
, p. 5947 - 5950 (2007/10/02)
Intramolecular Diels-Alder reaction of the triene 5 and Pd2+-promoted cyclization reaction of the olefinic silyl enol ether of 10 have been utilized as the key steps for a conceptually new, highly diastereocontrolled formal total synthesis of (
