Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
Org Lett. 2011 Apr 1;13(7):1820-3. doi: 10.1021/ol200333p. Epub 2011 Mar 3.
Intramolecular oxa-conjugate cyclization of α,β-unsaturated thioesters under Brønsted acid catalysis, inspired by biosynthesis of polyketide natural products, provides a variety of 2,6-cis-substituted tetrahydropyran derivatives with excellent diastereoselectivities. An added bonus of this methodology is that the product tetrahydropyrans could be readily elaborated to various derivatives by exploiting the unique reactivity of the thioester group.
受聚酮类天然产物生物合成的启发，在布朗斯特酸催化下，α,β-不饱和硫代酯的分子内氧杂共轭环化反应提供了多种具有优异非对映选择性的 2,6-顺式取代的四氢吡喃衍生物。该方法的一个额外优点是，通过利用硫酯基团的独特反应性，可以很容易地将产物四氢吡喃衍生化成各种衍生物。
