130115-07-0Relevant articles and documents
Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer
Peňa?ka, Tibor,Koukal, Petr,Kotora, Martin
, p. 147 - 149 (2018/01/27)
The key aetheramide A intermediate with the natural (R,R,R) configuration along with the one having the unnatural (R,S,R) configuration was synthesized. The synthesis of both stereoisomers was accomplished by Suzuki coupling of two advanced chiral building blocks: (R,R)- and (R,S)-vinylboronates and an (R)-iodoalkene. The former was prepared from (R)-mandelic acid, and the latter was prepared by enantioselective allylation of 3-iodoacrylaldehyde.
Catalyst-Controlled Multicomponent Aziridination of Chiral Aldehydes
Mukherjee, Munmun,Zhou, Yubai,Dai, Yijing,Gupta, AniL K.,Pulgam, V. Reddy,Staples, Richard J.,Wulff, William D.
, p. 2552 - 2556 (2017/03/06)
A highly diastereoselective and enantioselective method for the multicomponent aziridination of chiral aldehydes has been developed with BOROX catalysts of the VANOL (3,3′-diphenyl-2,2′-bi-1-naphthol) and VAPOL (2,2′-diphenyl-(4-biphenanthrol)) ligands. Very high to perfect catalyst control is observed with most all substrates examined including aldehydes with chiral centers in the α- and β-positions. High catalyst control was also observed for a number of chiral heterocyclic aldehydes allowing for the preparation of epoxy aziridines, bis(aziridines) and ethylene diaziridines. Application of this reaction in the synthesis of β3-homo-d-alloisoleucine and β3-homo-l-isoleucine is reported.
Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine
Liu, Cheng,Lin, Zhi-Wei,Zhou, Zhao-Hui,Chen, Hong-Bin
, p. 5395 - 5401 (2017/07/10)
Chiral amino alcohol-copper(ii) catalysts Cu-L1c and Cu-ent-L1c were utilized to promote the diastereoselective nitroaldol reactions of chiral aldehydes (S)-3 or (R)-3 with nitromethane, which respectively led to the preferential formation of certain stereoisomer for nitro diol derivatives 4. Using this catalytic protocol, all the four stereoisomers of the antidepressant reboxetine were divergently prepared. The highest overall yield of this synthetic route reached up to 30.5% from aldehyde (S)-3.
An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations
Richmond, Edward,Ling, Kenneth B.,Duguet, Nicolas,Manton, Lois B.,elebi-?lcüm, Nihan,Lam, Yu-Hong,Alsancak, Sezen,Slawin, Alexandra M. Z.,Houk,Smith, Andrew D.
, p. 1807 - 1817 (2015/02/19)
The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.
Concise stereoselective total synthesis of leiocarpin C
Chandra Rao, Dasireddi,Shekhar, Vanam,Kumar Reddy, Dorigondla,Chinnababu, Baggu,Venkateswarlu, Yenamandra
, p. 2179 - 2184 (2014/01/06)
A simple and highly concise strategy has been developed for the stereoselective total synthesis of leiocarpin C starting from commercially available mandelic ester. The strategy utilizes the OsO4-catalyzed cis-hydroxylation and selective reduction with K-Selectride as key steps. Copyright
Chemoenzymatic asymmetric synthesis of fluoxetine, atomoxetine, nisoxetine, and duloxetine
Rej, Rohan Kalyan,Das, Tapas,Hazra, Suman,Nanda, Samik
, p. 913 - 918 (2013/09/23)
The asymmetric synthesis of two well-known anti-depressant drugs, fluoxetine and duloxetine has been accomplished in a chemoenzymatic manner. The main highlight of the synthesis is the enantioselective cyanohydrin formation by a plant (R)-HNL (hydroxynitrile lyase). The enantiopure cyanohydrins are then synthetically manipulated into the above two drug molecules and two of their structural analogues, atomoxetine and nisoxetine.
First total synthesis of (+)-crassalactone A
Shekhar,Kumar Reddy,Suresh,Chanti Babu,Venkateswarlu
scheme or table, p. 946 - 948 (2010/04/29)
A simple and highly efficient first total synthesis of cytotoxic (+)-crassalactone A starting from (R)-mandelic acid is described. The strategy involves the osmium tetroxide-catalyzed cis-hydroxylation and the stereoselective addition of ethyl lithiopropi
Highly enantioselective hydrogenation of aryl vinyl ketones to allylic alcohols catalyzed by the tol-binap/Dmapen ruthenium(II) complex
Arai, Noriyoshi,Azuma, Keita,Nii, Noriyuki,Ohkuma, Takeshi
supporting information; experimental part, p. 7457 - 7460 (2009/03/12)
(Chemical Equation Presented) Binap catalyst doesn't dmapen expectations: In basified 2-propanol, [RuCl2{(S)-tol-binap}{(R)-dmapen}] (1, see picture, Ar=4-CH3C6H4) catalyzes the highly enantioselective hydrogenation of a series of aryl vinyl ketones and affords the allylic alcohols in high yields with up to 98% ee. Formation of the saturated ketones and alcohols is suppressed with triphenylphosphine when necessary.
Efficient and diastereoselective synthesis of (+)-goniobutenolide A via palladium-catalyzed ene-yne cross coupling-lactonization cascade
Kotora, Martin,Negishi, Ei-Ichi
, p. 9041 - 9042 (2007/10/03)
(+)-Goniobutenolide A was synthesized in six steps in 21.4% overall yield from (R)-mandelic acid via Pd-catalyzed ene-yne cross coupling-lactonization cascade with essentially complete control of the exocyclic alkene geometry. Copyright (C) 1996 Elsevier Science Ltd.
Concise total synthesis of (+)-goniofufurone and goniobutenolides A and B
Surivet, Jean-Philippe,Vatele, Jean-Michel
, p. 4373 - 4376 (2007/10/03)
Cytotoxic styryl lactones, (+)-goniofufurone and goniobutenolides A and B have been prepared in optically and diastereometically pure form from (R)-(- )-mandelic acid via the β-hydroxy sulfone 4 as a common intermediate.
