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.
All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry