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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)1396-1401
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number9
DOIs
Publication statusPublished - Mar 5 2021
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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