Silyl migrations in D-xylose derivatives: total synthesis of a marine quinoline alkaloid

Anuchit Phanumartwiwath; Thomas W Hornsby; Joazaizulfazli Jamalis; Christopher D Bailey; Christine L Willis

doi:10.1021/ol402760p

Silyl migrations in D-xylose derivatives: total synthesis of a marine quinoline alkaloid

Org Lett. 2013 Nov 15;15(22):5734-7. doi: 10.1021/ol402760p. Epub 2013 Oct 28.

Authors

Anuchit Phanumartwiwath¹, Thomas W Hornsby, Joazaizulfazli Jamalis, Christopher D Bailey, Christine L Willis

Affiliation

¹ School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, U.K.

PMID: 24229077
DOI: 10.1021/ol402760p

Abstract

A versatile method for the synthesis of orthogonally protected D-xylose 1-thioethers is described using unusual silyl group migrations which were pivotal in the synthesis of 4,8-dimethyl-6-O-(2',4'-di-O-methyl-β-D-xylopyranosyl)hydroxyquinoline confirming the structure and absolute configuration of the natural product.

Publication types

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

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Biological Products / chemistry
Hydroxyquinolines / chemical synthesis*
Hydroxyquinolines / chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Silanes / chemistry*
Xylose / analogs & derivatives*
Xylose / chemical synthesis*
Xylose / chemistry*

Substances

4,8-dimethyl-6-O-(2',4'-di-O-methyl-beta-D-xylopyranosyl)hydroxyquinoline
Alkaloids
Biological Products
Hydroxyquinolines
Silanes
Xylose