Total Synthesis of Marformycins A and D

被引：0
|
作者：
Anwar, Avraz F. [1 ]
Elbatrawi, Yassin M. [1 ]
Degen, David [2 ,3 ]
Ebright, Richard H. [2 ,3 ]
Del Valle, Juan R. [1 ]
机构：
[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
[2] Rutgers State Univ, Waksman Inst, Piscataway, NJ 08854 USA
[3] Rutgers State Univ, Dept Chem, Piscataway, NJ 08854 USA
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 46期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
NATURAL-PRODUCTS; ACID;
D O I：
10.1021/acs.orglett.4c04013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report the synthesis of the antimicrobial cyclodepsipeptides marformycin A (1) and marformycin D (2) using a solid-phase approach. A scalable solution-phase synthesis of the gamma-hydroxypiperazic acid subunit in 2, starting from cis-hydroxyproline, is also described. Structural analysis of 1 and its Leu-epi congener demonstrates conformational differences that may underlie their divergent antimicrobial activities. The described approach enables further development of conformation-activity relationships within this class of depsipeptide natural products.
引用
收藏
页码：10056 / 10060
页数：5
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