| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349034 | Tetrahedron: Asymmetry | 2010 | 4 Pages |
Abstract
An enantioselective intramolecular oxidative cyclization of 2-geranylphenols catalyzed by a Pd(II)-spiro bis(isoxazoline) complex is reported. The reaction proceeds in a 6-endo-trig manner to give chromene derivatives in reasonable yields and with moderate enantioselectivities. This transformation can be applied to a protecting-group-free total synthesis of naturally occurring cordiachromene.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(R)-6-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-benzopyran (cordiachromene)C16H20O2Ee = >54%[α]D25=-58.1 (c 0.04, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
Related Topics
Physical Sciences and Engineering
Chemistry
Inorganic Chemistry
Authors
Kazuhiro Takenaka, Yugo Tanigaki, Mahesh L. Patil, C.V. Laxman Rao, Shinobu Takizawa, Takeyuki Suzuki, Hiroaki Sasai,