Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9-and 10-methoxy derivatives

Authors
Sutherland, HS Higgs, KC Taylor, NJ Rodrigo, R
Citation
Hs. Sutherland et al., Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9-and 10-methoxy derivatives, TETRAHEDRON, 57(2), 2001, pp. 309-317
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
2
Year of publication
2001
Pages
309 - 317
Database
ISI
SICI code
0040-4020(20010107)57:2<309:IAOMIS>2.0.ZU;2-Y
Abstract
Syntheses of (+/-)-xestoquinone, (+/-)-9-methoxyxestoquinone and (+/-)-10-m ethoxyxestoquinone are described. A convergent CD plus ABE plan using the a ppropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemente d to provide these marine metabolites in overall yields of 18.3, 9.5 and 8. 5%, respectively. The latter pair of compounds, previously evaluated as inh ibitors of Topoisomerase II as an inseparable mixture, are now available se parate and pure for the first time. (C) 2000 Elsevier Science Ltd. All righ ts reserved.