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

K A Parker; A T Georges

doi:10.1021/ol991346l

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

Org Lett. 2000 Feb 24;2(4):497-9. doi: 10.1021/ol991346l.

Authors

K A Parker¹, A T Georges

Affiliation

¹ Department of Chemistry, Brown University, Providence, Rhode Island 02912, USA. kathlyn_parker@brown.edu

PMID: 10814360
DOI: 10.1021/ol991346l

Abstract

[reaction: see text] Nucleophilic 1,2-addition of lithiated glycal 9b to functionalized quinone 7 provided, after reductive aromatization, C-arylglycoside 11b. Treatment with mCPBA afforded the tricyclic papulacandin framework. Alternatively, hydroboration gave the chaetiacandin nucleus.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aminoglycosides*
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Carbohydrate Conformation
Carbohydrate Sequence
Echinocandins
Glycosides / chemical synthesis*
Hydroquinones / chemistry*
Molecular Sequence Data

Substances

Aminoglycosides
Anti-Bacterial Agents
Echinocandins
Glycosides
Hydroquinones
papulacandins
chaetiacandin