Efficient Diastereoselective Synthesis of (2R,3R,4R)-2-Amino-3-hydroxy-4,5-dimethylhexanoic Acid, the Lactone Linkage Unit of Homophymine A

Junpei Ohtaka; Akinari Hamajima; Tetsuhiro Nemoto; Yasumasa Hamada

doi:10.1248/cpb.c12-00944

Notes

Efficient Diastereoselective Synthesis of (2R,3R,4R)-2-Amino-3-hydroxy-4,5-dimethylhexanoic Acid, the Lactone Linkage Unit of Homophymine A

Junpei Ohtaka, Akinari Hamajima, Tetsuhiro Nemoto, Yasumasa Hamada

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Keywords: homophymine A, β-hydroxy-α-amino acid, anti-selective asymmetric hydrogenation, Evans’ asymmetric alkylation

JOURNAL FREE ACCESS

2013 Volume 61 Issue 2 Pages 245-250

DOI https://doi.org/10.1248/cpb.c12-00944

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Abstract

For the total synthesis of novel cyclodepsipeptide homophymine A, (2R,3R,4R)-2-amino-3-hydroxy-4,5-dimethylhexanoic acid was successfully synthesized by Evans’ asymmetric alkylation and the anti-selective asymmetric hydrogenation of a chiral α-amino-β-keto ester as the key steps.

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