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Observations on Dibutylstannylene as Template for the Assembly of Macrocyclic Oligolactones
Author(s) -
Bredenkamp Martin W.,
Flowers Harold M.,
Holzapfel Cedric W.
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250527
Subject(s) - chemistry , antiparallel (mathematics) , dimer , selectivity , stereochemistry , hexa , medicinal chemistry , catalysis , organic chemistry , physics , quantum mechanics , magnetic field
Dibutylstannylene‐mediated macrolactonization of methyl 4,6‐ O ‐benzylidene‐&7alpha;‐D‐glucopyranoside ( 2 ) with glutaryl and phthaloyl dichloride yields the respective dilactones 6e and 6f and parallel tetralactones 5e and 5f as well as the antiparallel tetralactone 4e in the case of glutarylation. The reaction with malonyl dichloride yields a negligible amount of the parallel tetralactone 5d and that of fumaryl and isophthaloyl dichloride yields polyesters only, a byproduct in all these reactions. The mechanism of stannylene‐medidted macrolactonization is discussed incorporating data pertaining to known hexa‐ and octalactone formation when succinyl dichloride is used. A correlation between stannylene dimer symmetry and tetralactone constitutional isomer selectivity is introduced.