The stereoselective synthesis of α-substituted β-amino secondary alcohols based on the proline-mediated, asymmetric, three-component Mannich reaction and its application to the formal total synthesis of nikkomycins B and Bx

Yujiro Hayashi, Tatsuya Urushima, Makoto Shin, Mitsuru Shoji

研究成果: Article査読

42 被引用数 (Scopus)

抄録

A general method for the asymmetric synthesis of α-substituted β-amino secondary alcohols is described, which comprises the four-reaction sequence (1) the proline-mediated, asymmetric, three-component Mannich reaction of two different aldehydes, (2) nucleophilic carbon addition to aldehyde, (3) oxidation of the resulting alcohol to the corresponding ketone, and (4) diastereoselective reduction with LiAlH(O-t-Bu)3 or catecholborane. The former reductant afforded the 1,2-syn isomer, while the latter gave the 1,2-anti isomer stereoselectively. The present method was successfully applied to the efficient asymmetric synthesis of the N-terminal amino acid moiety of nikkomycin B and BX.

本文言語English
ページ(範囲)11393-11404
ページ数12
ジャーナルTetrahedron
61
48
DOI
出版ステータスPublished - 2005 11 28

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

フィンガープリント 「The stereoselective synthesis of α-substituted β-amino secondary alcohols based on the proline-mediated, asymmetric, three-component Mannich reaction and its application to the formal total synthesis of nikkomycins B and B<sub>x</sub>」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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