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Volumn 68, Issue 7, 2003, Pages 2895-2902

Studies on the biosynthesis of paraherquamide A and VM99955. A theoretical study of intramolecular Diels-Alder cycloaddition

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER CYCLOADDITION;

EID: 0037419341     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020564g     Document Type: Article
Times cited : (37)

References (80)
  • 29
    • 0242474932 scopus 로고    scopus 로고
    • note
    • Syn/anti relationship refers to the relative stereochemistry between the C20 stereogenic center (paraherquamide A numbering) and the cyclic amino acid residue (proline or β-methylproline).
  • 30
    • 0242643331 scopus 로고    scopus 로고
    • note
    • α/β facial selectivity for the cyclization of the C14 methyl derivative 5 refers to the approach of the isoprene unit from the same or the opposite face containing the C14 methyl group, to distinguish it from the syn/anti selectivity in the formation of the C20 stereogenic center (see ref 8).
  • 63
    • 0003354199 scopus 로고
    • Geometry optimization on potential energy surface
    • Yarkony, D. R., Ed.; World Scientific Publishing: Singapore
    • (b) Schlegel, H. B. Geometry Optimization on Potential Energy Surface. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific Publishing: Singapore, 1994.
    • (1994) Modern Electronic Structure Theory
    • Schlegel, H.B.1
  • 70
    • 0242558635 scopus 로고    scopus 로고
    • note
    • 21 indicates that the actual charger transfer at the TS-inter is negligible (0.02 e), in agreement with a nonpolar process.16a
  • 71
    • 84962105974 scopus 로고
    • Diels-Alder reaction between butadiene and ethylene must be forced to take place: after 17 h at 165 °C and 900 atm, it does give a yield of 78%. Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98-122.
    • (1928) Justus Liebigs Ann. Chem. , vol.460 , pp. 98-122
    • Diels, O.1    Alder, K.2
  • 72
    • 0033832986 scopus 로고    scopus 로고
    • Similar result has been found for the unfavorable [5 + 2] cycloaddition of y-pyrones for which the lower negative activation entropy associated with the intramolecular process accounts for the facility of these cycloadditions. Domingo, L. R.; Zaragozá, R. J. J. Org. Chem. 2000, 65, 5480-5486.
    • (2000) J. Org. Chem. , vol.65 , pp. 5480-5486
    • Domingo, L.R.1    Zaragozá, R.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.