e-Journal

Abstract

1 data found. 1 - 1 listed
Paper | Special issue | Vol 90, No. 1, 2015, pp. 405 - 424
Published online: 13th June, 2014
DOI: 10.3987/COM-14-S(K)32
Stereoselective Approach toward Ophiodilactones Based on an Intramolecular [2 + 2] Cycloaddition Reaction

Takaaki Matsubara, Jun Ishihara, and Susumi Hatakeyama*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

The highly enantio- and diastereoselective synthesis of a promising precursor of ophiodilactones A and B, tetrameric phenylpropanoids isolated from the ophiuroid Ophiocoma scolopendrina, is described. The synthesis involves an organocatalytic asymmetric Michael reaction, intramolecular [2 + 2] cycloaddition of a ketene to an alkene, Baeyer-Villiger oxidation, and construction of the C2 quaternary center as major transformations.

Supporting Info. (1.3MB)Full Text HTMLPDF (949KB)PDF with Links (1.3MB)
1 data found. 1 - 1 listed