@article{6b0be74341aa4f269d3fa97880f44984,
title = "Asymmetric syntheses of diarylheptanoid natural products (-)-centrolobine and (-)-de-O-methylcentrolobine via hetero-Diels-Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate]",
abstract = "Catalytic asymmetric syntheses of (-)-centrolobine and (-)-de-O-methylcentrolobine have been achieved, incorporating a hetero-Diels-Alder (HDA) reaction between 4-aryl-2-silyloxy-1,3-butadienes and phenylpropargyl aldehyde derivatives as a key step. The HDA reaction using dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh2(R-BPTPI)4, as a chiral Lewis acid catalyst provides exclusively cis-2,6-disubstituted tetrahydropyran-4-ones in up to 93% ee.",
keywords = "(-)-Centrolobine, (-)-De-O-methylcentrolobine, Chiral Rh(II) catalyst, Diarylheptanoids, Hetero-Diels-Alder reaction",
author = "Takuya Washio and Reika Yamaguchi and Takumi Abe and Hisanori Nambu and Masahiro Anada and Shunichi Hashimoto",
note = "Funding Information: This research was supported, in part, by a Grant-in-Aid for Scientific Research on Priority Areas {\textquoteleft}Advanced Molecular Transformations of Carbon Resources{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan. T.W. is grateful to JSPS for a graduate fellowship. We thank Ms. S. Oka, M. Kiuchi, A. Maeda, and H. Matsumoto of the Center for Instrumental Analysis at Hokkaido University for mass measurements and elemental analysis.",
year = "2007",
month = nov,
day = "26",
doi = "10.1016/j.tet.2007.09.003",
language = "英語",
volume = "63",
pages = "12037--12046",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Ltd.",
number = "48",
}