Total synthesis of buergerinin F via effective construction of the asymmetric quaternary carbons using an enantioselective aldol reaction.
An efficient method for the synthesis of (+)-buergerinin F is established via the enantioselective aldol reaction of a tetra-substituted ketene silyl acetal with crotonaldehyde, followed by intramolecular Wacker-type ketalization.
Shiina
Isamu
I
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@ch.kagu.tus.ac.jp
Kawakita
Yo-ichi
Y
Ibuka
Ryoutarou
R
Yokoyama
Kazutoshi
K
Yamai
Yu-suke
YS
D000080:Acetals / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D000447:Aldehydes; D005030:Ethylenes; D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; D012821:Silanes; C479621:buergerinin F; D002244:Carbon; C116609:3-hydroxybutanal; C008223:ketene