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Volumn , Issue 28, 2009, Pages 4151-4165

Total synthesis and study of myrmicarin alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BRONSTED ACID; COPPER; DIMER; HETERODIMER; INDOLIZINE DERIVATIVE; MYRMICARIN ALKALOID; PALLADIUM; UNCLASSIFIED DRUG;

EID: 67650422535     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b903995n     Document Type: Review
Times cited : (23)

References (48)
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    • Exposure of a pure sample of M663 to air for 2 h results in 50% decomposition, while exposure of fresh poison gland secretion containing M430A to air for 1 h results in >90% decomposition of M430A (see refs. 1c and d). Due to overlap with the crosspeak signals of the tricyclic myrmicarins, the relative stereochemistry of C4a′ in M430A could not be determined from the NOESY spectrum by neutral alumina gel chromatography
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  • 12
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  • 14
    • 0346888810 scopus 로고
    • For computational analysis of fulvene FMOs, see: -369
    • K. N. Houk Acc. Chem. Res. 1975 8 361 369
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    • Houk, K.N.1
  • 24
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    • The absolute stereochemistry of the tricyclic and complex myrmicarins is based on their proposed biosynthetic relationship to M237A and M237B (see refs. 1a and 7) -667
    • S. Guindeuil S. Z. Zard Chem. Commun. 2006 665 667
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  • 29
    • 67650441937 scopus 로고    scopus 로고
    • Synthesized in two steps from l-glutamic acid diethylester hydrochloride
    • Synthesized in two steps from l-glutamic acid diethylester hydrochloride
  • 33
    • 1942533561 scopus 로고    scopus 로고
    • Z-β-Iodoenoates were prepared by treatment of the corresponding ynoates with sodium iodide in acetic acid at elevated temperatures (60-150 °C): -5823
    • M. P. Rainka Y. Aye S. L. Buchwald Proc. Natl. Acad. Sci. USA 2004 101 5821 5823
    • (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 5821
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  • 41
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    • While initial studies employed (S)-BINAP as a ligand according to the model for stereoinduction (see ref. 22), comparison of the optical rotation of 32 to the reported value (citref idrefs="cit16" position= "baseline"ref. 16) clarified the opposite sense of stereoinduction Following our initial report, an alternative synthesis of M215A involving formation of the C8 triisopropylbenzenesulfonylhydrazone followed by n-butyllithium-induced Shapiro reaction was developed, which provided M215A as a single diastereomer in 56% yield from the ketone 32 Heptacycle 50a may be in equilibrium with a corresponding trifluoroacetate adduct derivative Due to the oxidative sensitivity of these heptacyclic structures, attempts to prepare crystalline derivatives of isoM430A or protonated salts of the enamine 51 failed to yield samples suitable for X-ray analysis -5341
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  • 42
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    • DFT calculations performed using Spartan 2006, B3LYP/6-31G; gas-phase, energy minimized structure of the free azafulvenium ions
    • DFT calculations performed using Spartan 2006, B3LYP/6-31G; gas-phase, energy minimized structure of the free azafulvenium ions
  • 43
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    • 3 (0.30 equiv.) in the absence of M215B, 50% epimerization of the C8 alcohol occurred, suggesting reversible ionization and trapping Notably, M215B does not undergo homodimerization in the presence of acetic acid, suggesting that intramolecular alkylation of the hexacyclic azafulvenium ion 14 is more facile than intermolecular trapping of the tricyclic azafulvenium ion 1 by M215B
    • Whereas tether introduction had proceeded smoothly with the C9-epimeric diol, iterative silylation, deprotection of partially silylated material, and resubjection of the free diol was necessary to obtain significant quantities of the [1,3,2]-dioxasilocine product
  • 44
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    • 1H NMR analysis were unsuccessful. Heating to temperatures above 80°C led to decomposition For recent examples of palladium-mediated cyclizations onto pyrrole, see: -10097
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.