Stereoselective Synthesis of (2S,6R)‐Diamino‐(5R,7)‐dihydroxy‐heptanoic Acid (DADH): An Unusual Amino Acid from Streptomyces sp. SANK 60404
Stereoselective Synthesis of (2S,6R)‐Diamino‐(5R,7)‐dihydroxy‐heptanoic Acid (DADH): An Unusual Amino Acid from Streptomyces sp. SANK 60404
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(2S,6R)-二氨基-(5R,7)-二羟基庚酸 (DADH) 的立体选择性合成：来自链霉菌 SANK 60404 的一种不寻常氨基酸。
DOI：
10.1002/ejoc.202001646
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发表时间：
2021
影响因子：
2.8
通讯作者：
Shinada Tetsuro
中科院分区：
文献类型：
--
作者：
Okamura Hironori;Yasuno Yoko;Nakayama Atsushi;Takikawa Hirosato;Shinada Tetsuro
从链霉菌分离得到的生物合成前体(2S，6R)-二氨基-(5R，7)-二羟基-庚酸(DADH)的立体选择性合成。下沉60404是第一次实现。以加纳醛为手性源，通过DuPHOS-Rh催化脱氢氨基酸酯的不对称氢化反应，构建了DADH的三个立体中心。以加纳醛为原料，灵活地合成了DADH立体异构体，证明了该方法的合成优势。
Stereoselective synthesis of (2S,6R)‐diamino‐(5R,7)‐dihydroxy‐heptanoic acid (DADH), a biosynthetic precursor of vazabitide A, isolated fromStreptomycessp. 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.