Issue 8, 2004

Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols

Abstract

Tetrahydropyran and tetrahydrofuran containing natural products, drugs and agrochemicals often possess carbon–carbon bonds adjacent to the heteroatom. Consequently, new methods for the construction of anomeric carbon–carbon bonds are of considerable importance. We have devised a new strategy to access these systems that requires the treatment of O-glycoside alkynyl tributylstannane derivatives of furanyl and pyranyl lactols with Lewis acid to effect oxygen to carbon rearrangements. This leads to the formation of the corresponding carbon linked alkynol products that can be further manipulated to produce key structural motifs and building blocks for the assembly of complex molecules.

Graphical abstract: Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols

Supplementary files

Article information

Article type
Paper
Submitted
24 Dec 2003
Accepted
23 Feb 2004
First published
18 Mar 2004

Org. Biomol. Chem., 2004,2, 1145-1154

Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols

M. F. Buffet, D. J. Dixon, S. V. Ley, D. J. Reynolds and R. I. Storer, Org. Biomol. Chem., 2004, 2, 1145 DOI: 10.1039/B316858A

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