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]

Takuya Washio; Reika Yamaguchi; Takumi Abe; Hisanori Nambu; Masahiro Anada; Shunichi Hashimoto

doi:10.1016/j.tet.2007.09.003

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]

Takuya Washio, Reika Yamaguchi, Takumi Abe, Hisanori Nambu, Masahiro Anada, Shunichi Hashimoto

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

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.

Original language	English
Pages (from-to)	12037-12046
Number of pages	10
Journal	Tetrahedron
Volume	63
Issue number	48
DOIs	https://doi.org/10.1016/j.tet.2007.09.003
Publication status	Published - Nov 26 2007
Externally published	Yes

Keywords

(-)-Centrolobine
(-)-De-O-methylcentrolobine
Chiral Rh(II) catalyst
Diarylheptanoids
Hetero-Diels-Alder reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Washio, T., Yamaguchi, R., Abe, T., Nambu, H., Anada, M., & Hashimoto, S. (2007). 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]. Tetrahedron, 63(48), 12037-12046. https://doi.org/10.1016/j.tet.2007.09.003

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]. / Washio, Takuya; Yamaguchi, Reika; Abe, Takumi et al.
In: Tetrahedron, Vol. 63, No. 48, 26.11.2007, p. 12037-12046.

Research output: Contribution to journal › Article › peer-review

Washio, T, Yamaguchi, R, Abe, T, Nambu, H, Anada, M & Hashimoto, S 2007, '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]', Tetrahedron, vol. 63, no. 48, pp. 12037-12046. https://doi.org/10.1016/j.tet.2007.09.003

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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 = "English",

volume = "63",

pages = "12037--12046",

journal = "Tetrahedron",

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T1 - 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]

AU - Washio, Takuya

AU - Yamaguchi, Reika

AU - Abe, Takumi

AU - Nambu, Hisanori

AU - Anada, Masahiro

AU - Hashimoto, Shunichi

N1 - Funding Information: This research was supported, in part, by a Grant-in-Aid for Scientific Research on Priority Areas ‘Advanced Molecular Transformations of Carbon Resources’ 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.

PY - 2007/11/26

Y1 - 2007/11/26

N2 - 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.

AB - 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.

KW - (-)-Centrolobine

KW - (-)-De-O-methylcentrolobine

KW - Chiral Rh(II) catalyst

KW - Diarylheptanoids

KW - Hetero-Diels-Alder reaction

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U2 - 10.1016/j.tet.2007.09.003

DO - 10.1016/j.tet.2007.09.003

M3 - Article

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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

Keywords

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