Enantioselective synthesis of (-)-kainic acid

Takano, Seiichi; Sugihara, Takumichi; Satoh, Shigeki; Ogasawara, Kunio

doi:10.1021/ja00227a029

Cited by 71 publications

(28 citation statements)

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“…The synthesis of 14 via a different route has been described. [46] Our analytical data are in agreement with those reported.…”

Section: Benzyl (2s3s4s)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isosupporting

confidence: 91%

“…[46] [a] X-ray data were collected on a Bruker APEX (6l and 7c), a Bruker Smart CCD (6g and 7b) area detector diffractometer using graphite-monochromated Mo-Ka radiation (l = 0.71073 ) and 0.38 w-scan frames or on an Oxford Xcalibur (6d) diffractometer with Cu Nova Microsource and Onyx detector using Cu-Ka radiation (l = 1.54184 ) and 1.08 wscan frames. Intensities were corrected for Lorentz and polarization effects, an empirical absorption correction was applied using SADABS [52] based on the Laue symmetry of the reciprocal space.…”

Section: Benzyl (2s3s4s)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isomentioning

confidence: 99%

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Bicyclic Cyclopentenones via the Combination of an Iridium‐ Catalyzed Allylic Substitution with a Diastereoselective Intramolecular Pauson–Khand Reaction

et al. 2011

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Enantioselective syntheses of bicyclic cyclopentenones are described. Key steps are an iridium-catalyzed allylic substitution and an intramolecular diastereoselective Pauson-Khand reaction. The diastereoselectivity of the Pauson-Khand reaction was found to be crucially dependent on the unit connecting the propargylic and the olefinic parts of the precursor. Very high degrees of diastereoselection were obtained with an NBoc unit as connector. This methodology has been illustrated by application within an enantioselective formal total synthesis of (À)-a-kainic acid.

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“…The synthesis of 14 via a different route has been described. [46] Our analytical data are in agreement with those reported.…”

Section: Benzyl (2s3s4s)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isosupporting

confidence: 91%

Section: Benzyl (2s3s4s)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isomentioning

confidence: 99%

Bicyclic Cyclopentenones via the Combination of an Iridium‐ Catalyzed Allylic Substitution with a Diastereoselective Intramolecular Pauson–Khand Reaction

et al. 2011

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“…Five-membered oxygen-or nitrogenated heterocycles are important intermediates for the synthesis of pharmaceutically and biologically active molecules, such as (À)-domoic acid, [4] isodomoic acid H, [5] kainic acid, [6] conessine, [7] and (+)-intricarene.…”

Section: Introductionmentioning

confidence: 99%

“…Note, product 2 is an important structural unit and is easily modified to a natural product, such as kainic acid. [6] Results and Discussion…”

Section: Introductionmentioning

confidence: 99%

Brønsted Acid Catalyzed Cyclization of Hydroxylated Enynes: A Concise Synthesis of Five‐Membered Heterocycles

Chen

Zhu

et al. 2010

Chemistry A European J

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A mild and direct pathway for the formation of five-membered heterocyclic compounds from hydroxylated enynes has been developed. In this reaction, hydroxylated enynes were selectively transformed into five-membered heterocyclic compounds 2, with an allene moiety at the 3-position, in the presence of F(3) CSO(3) H (0.1 mol %). When R(1) , R(2) =Ph, diphenylvinyl-2,3-dihydro-1H-pyrrole (2 y) was obtained. With HSbF(6) (5 mol %) as the catalyst, polycyclic skeletons 3 and 4 with adjacent stereocenters were obtained. When R(1) =H and R(2) =styrene, 1,3-dienyl-2,5-dihydro-1H-pyrrole (6 as) was formed. This Brønsted acid catalyzed domino process involves the formation of an allene carbocation intermediate, which can be readily trapped by olefins to give various novel five-membered heterocyclic skeletons.

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“…Enantiomerically pure syn-and anti-2-amino-1,3,4-trihydroxy-butane 1 and syn-and anti-2-azido-1,3,4-trihydroxy-butane 2 (Fig. 1) would be interesting chiral building blocks in the synthesis of several important compounds such as sphingosines, 1 FR900482 an antitumour antibiotic, 2 kainic acid, 3 liposidomycins 4 and glycomimetics. 5 Particularly, such compounds can be used for the synthesis of C4 unit of Nelfinavir, one of the most potent HIV-protease inhibitors (Fig.…”

Section: Introductionmentioning

confidence: 99%

Lipase-catalyzed resolution of anti-6-substituted 1,3-dioxepan-5-ols

Gruttadauria

Meo

Riela

et al. 2006

Tetrahedron: Asymmetry

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Abstract-Several anti-6-substituted 1,3-dioxepan-5-ols were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30°C. This approach provided, in some cases, the alcohol and the acetate in high enantiomeric purity, depending on the nature of the substituent (R = N 3 , SePh, I, OBn) and the acetal group (unsubstituted or dimethyl). The role of the size of substituents is also discussed. Enantiopure anti-6-substituted 1,3-dioxepan-5-ols are useful building blocks.

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Enantioselective synthesis of (-)-kainic acid

Cited by 71 publications

References 0 publications

Bicyclic Cyclopentenones via the Combination of an Iridium‐ Catalyzed Allylic Substitution with a Diastereoselective Intramolecular Pauson–Khand Reaction

Bicyclic Cyclopentenones via the Combination of an Iridium‐ Catalyzed Allylic Substitution with a Diastereoselective Intramolecular Pauson–Khand Reaction

Brønsted Acid Catalyzed Cyclization of Hydroxylated Enynes: A Concise Synthesis of Five‐Membered Heterocycles

Lipase-catalyzed resolution of anti-6-substituted 1,3-dioxepan-5-ols

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