Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide.
作者： Robert M. Adlington , Jack E. Baldwin , Alexander V. W. Mayweg , Gareth J. Pritchard
DOI: 10.1021/OL026467R
关键词:
摘要: A study toward a possible biomimetic hetero Diels−Alder reaction is reported between humulene and novel tropolone ortho-quinone methide. suitable methide precursor has been prepared from 3-methyl-2-furoate. Heating the gave methide, which in presence of underwent to give deoxy analogue epolone B.
acs.org
sci-hub.se 参考文章(8)
James B. Hendrickson, James S. Farina, A new 7-ring cycloaddition reaction Journal of Organic Chemistry. ,vol. 11, pp. 3359- 3361 ,(1980) , 10.1021/JO01304A047
Jack E. Baldwin, Alexander V. W. Mayweg, Karin Neumann, Gareth J. Pritchard, Studies toward the biomimetic synthesis of tropolone natural products via a hetero Diels-Alder reaction. Organic Letters. ,vol. 1, pp. 1933- 1935 ,(1999) , 10.1021/OL991067Y
Guy H. Harris, Karst Hoogsteen, Keith C. Silverman, Susan L. Raghoobar, Gerald F. Bills, Russell B. Lingham, Jack L. Smith, Harry W. Dougherty, Carmen Cascales, Fernando Peláez, Isolation and structure determination of pycnidione, a novel bistropolone stromelysin inhibitor from a Phoma sp. Tetrahedron. ,vol. 49, pp. 2139- 2144 ,(1993) , 10.1016/S0040-4020(01)80357-4
FRIEDRICH MAYERL, QI GAO, STELLA HUANG, STEVEN E. KLOHR, JAMES A. MATSON, DONALD R. GUSTAVSON, DOLORES M. PIRNIK, RONALD L. BERRY, CRAIG FAIRCHILD, WILLIAM C. ROSE, Eupenifeldin, a novel cytotoxic bistropolone from Eupenicillium brefeldianum. The Journal of Antibiotics. ,vol. 46, pp. 1082- 1088 ,(1993) , 10.7164/ANTIBIOTICS.46.1082
Naoki Ohmori, Synthetic study of phomoidride B (CP-263,114); utilization of the oxidopyrylium [5 + 2] cycloaddition Chemical Communications. pp. 1552- 1553 ,(2001) , 10.1039/B104268H
Tatsuya ITO, Tadashi ARAI, Yuji OHASHI, Yoshio SASADA, Structure of Fusariocin C, A Cytotoxic Metabolite from Fusarium Moniliforme Agricultural and biological chemistry. ,vol. 45, pp. 1689- 1692 ,(1981) , 10.1271/BBB1961.45.1689
Ping Cai, David Smith, Bernadette Cunningham, Sheryl Brown-Shimer, Barry Katz, Cedric Pearce, Debra Venables, David Houck, None, Epolones: Novel Sesquiterpene-Tropolones from Fungus OS-F69284 That Induce Erythropoietin in Human Cells Journal of Natural Products. ,vol. 61, pp. 791- 795 ,(1998) , 10.1021/NP9800506
Tatsuya ITÔ, Fusariocin C, a new cytotoxic substance produced by Fusarium moniliforme. Agricultural and biological chemistry. ,vol. 43, pp. 1237- 1242 ,(1979) , 10.1271/BBB1961.43.1237