An enantiospecific total synthesis of (–)-α-kainic acid

Cooper, Jeremy; Knight, David W.; Gallagher, P. T.

doi:10.1039/c39870001220

Cited by 46 publications

(12 citation statements)

References 2 publications

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“…Hydrogenolysis of the benzyl ester (-)-15 afforded the L-proline derivative (-)-14 in 89 YO yield and with an enantiomeric purity of > 99 YO ee, as determined by gas chromatography for its methyl-ester derivative. The specific rotation of (-)-I4 was found to be significantly higher than that reported by Cooper et al [14] for the enantiomeric (+)-14, indicating their product to have only ca. 80% ee.…”

contrasting

confidence: 74%

“…The (2R,3S)-enantiomer (+)-14 was obtained in the lower-melting crystal modification, i.e., with m.p. 106-107", and showed exactly the opposite specific rotation of (-)-I4 Both (-)-14 and (+)-14 exceeded considerably the optical rotations so far reported [14].…”

mentioning

confidence: 55%

“…[aID = -97 (c = 1, H20) ( [21]: c = 1, H,O)). Based on these data, the material described by Cooper et al [14] appears to have an enantiomeric purity (ee) of ca. 80%.…”

Section: Cis-n-(tert-butoxycarbonyl-3-hydroxy-d-proline ((+)-14)mentioning

confidence: 94%

“…To this Cooperet af. [14] reported (+)-14 with a m.p. of 101-103" and [a], = +55.5 (c = 1.39, CH,CI,).…”

Section: Cis-n-(tert-butoxycarbonyl-3-hydroxy-d-proline ((+)-14)mentioning

confidence: 97%

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Total Synthesis of Cyclothialidine

Götschi

Jenny

Reindl

et al. 1996

Helvetica Chimica Acta

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A total synthesis of cyclothialidine (l), a new DNA gyrase inhibitor isolated from Streptomycesfilipinensis, is described. The synthetic concept was tested by preparing the lactone 13 (Scheme 2) which contains the characteristic bicyclic core entity of 1. Key features of the synthesis of 1 are: preparation of 3,5-dihydroxy-2,6-dimethylbenzoic acid (23) from 3,5-dihydroxybenzoic acid (19) by two consecutive Mannich aminomethylation/hydrogenation sequences; benzylic N-bromosuccinimide bromination of an ester derivative 25 thereof and its subsequent coupling with Boc-Ser-Cys-OMe (11); cyclization of the o-hydroxy acid 29 to the 12-membered lactone 30 using preferably Mitsunobu conditions; completion of the peptidic side chains of 1 using Boc strategy (Scheme 4 ) . Optically pure cis-N-(ter~-butoxycarbonyl)-3-hydroxy-~-proline ((-)-14) was obtained by resolution of the racemate via an efficient reaction sequence containing a lipase-catalyzed enantiospecific acetate hydrolysis (Scheme 3 ) . The structure of natural 1 was confirmed by comparison with the synthetic material. The synthetic route described provides also easy access to analogues of 1, e.g., via the intermediate 30.

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contrasting

confidence: 74%

mentioning

confidence: 55%

“…[aID = -97 (c = 1, H20) ( [21]: c = 1, H,O)). Based on these data, the material described by Cooper et al [14] appears to have an enantiomeric purity (ee) of ca. 80%.…”

Section: Cis-n-(tert-butoxycarbonyl-3-hydroxy-d-proline ((+)-14)mentioning

confidence: 94%

“…To this Cooperet af. [14] reported (+)-14 with a m.p. of 101-103" and [a], = +55.5 (c = 1.39, CH,CI,).…”

Section: Cis-n-(tert-butoxycarbonyl-3-hydroxy-d-proline ((+)-14)mentioning

confidence: 97%

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Total Synthesis of Cyclothialidine

Götschi

Jenny

Reindl

et al. 1996

Helvetica Chimica Acta

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“…The relative configuration of the major diastereomer (rac-46) was assigned by NOESY NMR spectroscopy (NOE between the protons of the OMe group at C-11 and H-3'). Global oxidation of rac-46 with Jones reagent [55] at 0 8C directly afforded the cyclo-mumbaiststain derivative rac-47 in 59 % yield under liberation of the anthraquinone substructure and installation of the carboxyl group at the end of the side chain.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Total Synthesis of cyclo‐Mumbaistatin Analogues through Anionic Homo‐Fries Rearrangement

Neufeind

Hülsken

Neudörfl

et al. 2011

Chemistry A European J

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The structurally unique polyketide mumbaistatin is the strongest naturally occurring inhibitor of glucose-6-phosphate translocase-1 (G6P-T1), which is a promising target for drugs against type-2 diabetes mellitus and angiogenic processes associated with brain tumor development. Despite its high relevance, mumbaistatin has so far withstood all attempts towards its total synthesis. In the present study an efficient total synthesis of a deoxy-mumbaistatin analogue containing the complete carbon skeleton and a spirolactone motif closely resembling the natural product in its cyclized form was elaborated. Key steps of the synthesis are a Diels-Alder cycloaddition for the construction of the fully functionalized anthraquinone moiety and an anionic homo-Fries rearrangement to build up the tetra-ortho-substituted benzophenone core motif, from which a spiroketal lactone forms in a spontaneous process. The elaborated strategy opens an entry to a variety of new analogs of mumbaistatin and cyclo-mumbaistatin and may be exploited for the total synthesis of the natural product itself in the future.

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