A one-pot chemoenzymatic synthesis of (2S, 4R)-4-methylproline enables the first total synthesis of antiviral lipopeptide cavinafungin B

被引：13

作者：

Zwick, Christian R., III ^{[1
]}

Renata, Hans ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, 130 Scripps Way, Jupiter, FL 33458 USA

来源：

TETRAHEDRON | 2018年 / 74卷 / 45期

关键词：

Biocatalysis; Lipopeptide; Chemoenzymatic synthesis; Hydroxylation; SOLID-PHASE SYNTHESIS; NATURAL-PRODUCTS; ANTIBIOTICS; PEPTIDES; PERSPECTIVE; INHIBITORS; DISCOVERY; ALDEHYDES; PROLINES; ANALOGS;

D O I：

10.1016/j.tet.2018.09.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient ten-step (longest linear sequence) synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (AT (Boc)G-Rink resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner. This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：6469 / 6473

页数：5

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