Synthesis of polyketides via diastereoselective acetalization.
[reaction: see text] Diastereoselective acetalization of pseudo-C(2)-symmetric 1,3,5-triol systems is a general strategy for the rapid generation of polyketides. The oxidative acetalization reaction shown above was studied under both kinetic and thermodynamic conditions, using synthetic 1,3,5-triol units. In addition, all possible stereochemical variants of a 1,3,5-triol system were prepared from the corresponding acetal to expand the synthetic versatility of this method.
Shepherd
Jennifer N
JN
Department of Chemistry, Gonzaga University, Spokane, Washington 99258, USA. shepherd@gonzaga.edu
Myles
David C
DC
D000080:Acetals / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000080:Acetals; D007659:Ketones