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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.