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Volumn 17, Issue 36, 2011, Pages 10123-10134

Conception, synthesis, and biological evaluation of original discodermolide analogues

Author keywords

anticancer agents; cross coupling; discodermolide; nickel; polyketides

Indexed keywords

ANTI-CANCER AGENTS; BIOLOGICAL ACTIVITIES; BIOLOGICAL EVALUATION; CROSS-COUPLINGS; DISCODERMOLIDE; METHYL GROUP; NANOMOLAR RANGE; POLYKETIDES; SYNTHETIC ANALOGUES; TOTAL SYNTHESIS;

EID: 80051975900     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100675     Document Type: Article
Times cited : (10)

References (107)
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    • For a preparative scale synthesis of DDM, see
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    • It has been shown by stochastic conformational analysis (Monte Carlo method, Spartan′04 Win. Software, MMF94aq force field) from RX diffraction DDM structure, that the "U"-shaped conformers of the three following analogues were the lowest in energy (see the Supporting Information).
    • It has been shown by stochastic conformational analysis (Monte Carlo method, Spartan′04 Win. Software, MMF94aq force field) from RX diffraction DDM structure, that the "U"-shaped conformers of the three following analogues were the lowest in energy (see the Supporting Information).
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    • Noteworthy, in this particular case, the vinylation reaction of 11 with vinylmagnesium bromide gave highly variable but mostly low yields. The reaction with solely vinyllithium species without magnesium salt (produced from tetravinyltin and MeLi) allowed the formation of the desired product 12 in a reproducible high yield.
    • Noteworthy, in this particular case, the vinylation reaction of 11 with vinylmagnesium bromide gave highly variable but mostly low yields. The reaction with solely vinyllithium species without magnesium salt (produced from tetravinyltin and MeLi) allowed the formation of the desired product 12 in a reproducible high yield.
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    • The assignment of the configuration of the (S)-C12 methyl centre of compound 25 was determined in analogy with the corresponding sequence developed for DDM synthesis.
    • The assignment of the configuration of the (S)-C12 methyl centre of compound 25 was determined in analogy with the corresponding sequence developed for DDM synthesis.
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    • In this case, the Suzuki cross-coupling reaction gave a highly disappointing low yield (10 %). We suspected that the isopropyl group could have deleterious effects for steric reasons. Therefore, we investigated this reaction between model substrates; however, under the same conditions; the desired product was obtained in 61 % yield.
    • In this case, the Suzuki cross-coupling reaction gave a highly disappointing low yield (10 %). We suspected that the isopropyl group could have deleterious effects for steric reasons. Therefore, we investigated this reaction between model substrates; however, under the same conditions; the desired product was obtained in 61 % yield.
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    • The formation of the cyclohexene 40 through an intramolecular coupling reaction proves the fold of the C8-C14 core.
    • The formation of the cyclohexene 40 through an intramolecular coupling reaction proves the fold of the C8-C14 core.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.