Reductive aromatization of quinols: Synthesis of the C-arylglycoside nucleus of the papulacandins and chaetiacandin

Authors
Parker, KA Georges, AT
Citation
Ka. Parker et At. Georges, Reductive aromatization of quinols: Synthesis of the C-arylglycoside nucleus of the papulacandins and chaetiacandin, ORG LETT, 2(4), 2000, pp. 497-499
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
4
Year of publication
2000
Pages
497 - 499
Database
ISI
SICI code
1523-7060(20000224)2:4<497:RAOQSO>2.0.ZU;2-C
Abstract
[GRAPHICS] Nucleophilic 1,2-addition of lithiated glycal 9b to functionalized quinone 7 provided, after reductive aromatization, C-arylglycoside 11b. Treatment w ith mCPBA afforded the tricyclic papulacandin framework. Alternatively, hyd roboration gave the chaetiacandin nucleus.