Synthetic microbial chemistry XXXII - Synthesis and absolute configurationof hongoquercin A, an antibacterial sesquiterpene-substituted orsellinic acid isolated as a fungal metabolite

Authors
Tsujimori, H Bando, M Mori, K
Citation
H. Tsujimori et al., Synthetic microbial chemistry XXXII - Synthesis and absolute configurationof hongoquercin A, an antibacterial sesquiterpene-substituted orsellinic acid isolated as a fungal metabolite, EUR J ORG C, (2), 2000, pp. 297-302
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
2
Year of publication
2000
Pages
297 - 302
Database
ISI
SICI code
1434-193X(200001):2<297:SMCX-S>2.0.ZU;2-M
Abstract
(+/-)-Hongoquercin A (1), the racemate of an antibacterial fungal metabolit e, has been synthesized starting from geranylacetone (2) and ethyl orsellin ate (ethyl 2,4-dihydroxy-6-methylbenzoate, 5). The structure (+/-)-1 has be en confirmed by X-ray analysis of its ethyl ester (+/-)-10. Synthesis of th e naturally occurring (+)-hongoquercin A from (-)-sclareol (11) established its configuration as depicted in 1.