An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin
An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.
THE SYNTHESIS AND REACTIVITY OF 5-NITRO-2-FURYLACETYLENE
This paper describes the preparation of 5-nitro-2-furylacetylene (I), the starting material for the synthesis 1-iodo-2-(5-nitro-2-furyl)ethylene (II), 3-(5-nitro-2-furyl)propionic acid (III) and 1,2-bis-(5-nitro-2-furyl)-acetylene (IX), substance possessing antibacterial properties.
Vegh, Daniel,Kovac, Jaroslav
p. 280 - 284
(2007/10/02)
5-Nitro-2-furylvinylation of Secondary and Tertiary Amines
Reaction of 12 secondary amines and trimethylamine with (Z) and (E)-5-nitro-2-furylvinylbromide (I) was studied.Whereas the enamine II, obtained from secondary amines, have the E configuration, the quaternisation of trimethyamine affords stereospecifically the corresponding (Z) or (E) vinylammonium salts III.