期刊
TETRAHEDRON
卷 66, 期 52, 页码 9894-9901出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.10.057
关键词
Quantum-chemical CD calculations; Isolation of marine natural products; Structure elucidation; Sorbicillinol derivatives; Attribution of absolute configuration
资金
- German Bundesministerium fur Bildung, Wissenschaft und Forschung (BMBF) [03F0345E, 03F0345B, 03F0345A]
- Deutsche Forschungsgemeinschaft [Br 699/13-5, SFB 630]
- Ministry of Science, Economic Affaires and Transport of the State of Schleswig-Holstein (Germany)
Three novel natural products, sorbifuranones A-C (4-6), were isolated from a Penicillium cluysogenum fungus isolated from the marine sponge Ircinia fasciculata. Sorbifuranones B (5) and C (6) and 2',3'-dihydrosorbicillin, a putative precursor to sorbifuranone B, were also found in the culture of another Penicillium strain, which was isolated from the sponge Tethya aurantium. Their constitutions were elucidated mainly by 2D NMR. NOE correlations in combination with quantum chemical calculations and comparison of experimental and calculated electronic circular dichroism (CD) spectra permitted assignment of the absolute configuration of sorbifuranone C. The structures hint at a two-step cleavage-cyclization sequence of sorbifuranone A (4) leading to the Spiro compound sorbifuranone C, while sorbifuranone B is likely to be the respective cleavage product of a putative 2',3'-dihydrosorbifuranone A, which cannot cyclize further. (C) 2010 Elsevier Ltd. All rights reserved.
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