Stereoselective Synthesis of (2S,6R)-Diamino-(5R,7)-dihydroxy-heptanoic Acid (DADH): An Unusual Amino Acid from Streptomyces sp. SANK 60404

Hironori Okamura, Yoko Yasuno, Atsushi Nakayama, Hirosato Takikawa, Tetsuro Shinada

研究成果: Contribution to journalArticle査読

抄録

Stereoselective synthesis of (2S,6R)-diamino-(5R,7)-dihydroxy-heptanoic acid (DADH), a biosynthetic precursor of vazabitide A, isolated from Streptomyces sp. SANK 60404 was achieved for the first time. Three stereogenic centers of DADH were constructed by the chemical manipulation on Garner's aldehyde as a chiral source and DuPHOS-Rh-catalyzed asymmetric hydrogenation of a dehydroamino acid ester. The synthetic advantage of the present method was demonstrated by the flexible synthesis of the DADH stereoisomers from Garner's aldehyde.

本文言語英語
ページ(範囲)1396-1401
ページ数6
ジャーナルEuropean Journal of Organic Chemistry
2021
9
DOI
出版ステータス出版済み - 3 5 2021
外部発表はい

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

フィンガープリント 「Stereoselective Synthesis of (2S,6R)-Diamino-(5R,7)-dihydroxy-heptanoic Acid (DADH): An Unusual Amino Acid from Streptomyces sp. SANK 60404」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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