Synthesis of delta-tributylstannyl-alpha,beta,gamma,delta-unsaturated aldehydes from pyridines.
Zincke aldehydes, which are readily available from the ring-opening reaction of pyridinium salts, are easily converted into delta-tributylstannyl-alpha,beta,gamma,delta-unsaturated aldehydes (stannyldienals) by the action of tributylstannyllithium. This reaction appears to proceed via 1,6-stannyllithium addition/elimination of lithium dialkylamide. Several stannyldienals of significant utility for the synthesis of polyene natural products have been made by this route, which proceeds in modest yields, but is successful on multigram scale using inexpensive reagents. Simple stannylenals and stannylenones are similarly available from the corresponding vinylogous amides.
Michels
Theo D
TD
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Rhee
Jong Uk
JU
Vanderwal
Christopher D
CD
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002073:Butanes / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D017971:Tin Compounds / Q000737:chemistry*
D000447:Aldehydes; D002073:Butanes; D011725:Pyridines; D017971:Tin Compounds