New syntheses of the benzoquinone primin and its water-soluble analog primin acid via Heck reactions

Authors
Mabic, S Vaysse, L Benezra, C Lepoittevin, JP
Citation
S. Mabic et al., New syntheses of the benzoquinone primin and its water-soluble analog primin acid via Heck reactions, SYNTHESIS-S, (7), 1999, pp. 1127-1134
Citations number
52
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
7
Year of publication
1999
Pages
1127 - 1134
Database
ISI
SICI code
0039-7881(199907):7<1127:NSOTBP>2.0.ZU;2-D
Abstract
The syntheses of primin, 2-methoxy-6-pentylbenzoquinone (1), a major allerg en of Primula obconica and its water-soluble acid analog primin acid (2) ar e reported. The key steps were ortho-lithiation reactions of protected hydr oquinones, palladium coupling (Heck) reactions, and salcomine-catalyzed oxi dations of phenols to quinones.