56850-02-3Relevant academic research and scientific papers
Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of lactols
Buffet, Marianne F.,Dixon, Darren J.,Ley, Steven V.,Tate, Edward W.
, p. 1091 - 1092 (1998)
Treatment of alkynyl tributylstannane tetrahydropyranyl and tetrahydrofuranyl ether derivatives with boron trifluoride etherate effects an efficient anomeric oxygen to carbon rearrangement leading to the corresponding carbon-linked alkynol products.
Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols
Buffet, Marianne F.,Dixon, Darren J.,Ley, Steven V.,Reynolds, Dominic J.,Storer, R. Ian
, p. 1145 - 1154 (2007/10/03)
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.
A SYNTHESIS OF 1,6-DIOXASPIRODEC-3-ENES.
Whitby, Richard,Kocienski, Philip
, p. 3619 - 3622 (2007/10/02)
Base-catalysed rearrangement of a 2-alkynyl-tetrahydropyran generates an allenol ether intermediate which undergoes acid-catalysed cyclisation to the 1,6-dioxaspirodec-3-ene system.
