Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A

Akihiro Sakama, Yoshiyasu Nishimura, Yuko Motohashi, Keisuke Yoshida, Kenichi Takao

研究成果: Article

抄録

Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

元の言語English
ページ(範囲)5465-5471
ページ数7
ジャーナルTetrahedron
72
発行部数35
DOI
出版物ステータスPublished - 2016 9 1

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Aldehydes
Carbon
Sugars
vibsanin A

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes : synthesis of a fragment of (+)-vibsanin A. / Sakama, Akihiro; Nishimura, Yoshiyasu; Motohashi, Yuko; Yoshida, Keisuke; Takao, Kenichi.

:: Tetrahedron, 巻 72, 番号 35, 01.09.2016, p. 5465-5471.

研究成果: Article

Sakama, Akihiro ; Nishimura, Yoshiyasu ; Motohashi, Yuko ; Yoshida, Keisuke ; Takao, Kenichi. / Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes : synthesis of a fragment of (+)-vibsanin A. :: Tetrahedron. 2016 ; 巻 72, 番号 35. pp. 5465-5471.
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T1 - Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes

T2 - synthesis of a fragment of (+)-vibsanin A

AU - Sakama, Akihiro

AU - Nishimura, Yoshiyasu

AU - Motohashi, Yuko

AU - Yoshida, Keisuke

AU - Takao, Kenichi

PY - 2016/9/1

Y1 - 2016/9/1

N2 - Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

AB - Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

KW - Allylation

KW - Boronates

KW - Carbohydrates

KW - Diastereoselectivity

KW - Quaternary stereocenter

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