Synthesis of More Highly Oxidized Alkyl Citrates via Direct Regio- and Stereoselective Oxidation

被引：1

作者：

Rossouw, Nikolai P. ^{[1
]}

Chen, Zongjia ^{[1
]}

White, Jonathan M. ^{[1
]}

Rizzacasa, Mark A. ^{[1
]}

机构：

[1] Univ Melbourne, Bio21 Mol Sci & Biotechnol Inst, Sch Chem, Melbourne, Vic 3010, Australia

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 44期

基金：

澳大利亚研究理事会;

关键词：

ZARAGOZIC-ACID; ENANTIOSPECIFIC SYNTHESIS; (-)-CINATRIN C-1; INHIBITORS; ESTER;

D O I：

10.1021/acs.orglett.3c03232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to more highly oxidized alkyl citrates by direct regio- and stereoselective oxidations is reported. The total synthesis and structural assignment of alkyl citrate L-731-128 are described, and the synthesis of its C4 oxidized congener L-731,127 utilized a regio- and stereoselective enolate oxidation with oxygen gas. A highly stereoselective Rubottom oxidation of a cyclic silylketene acetal then enabled oxidation at C2 to afford the cinatrins C-1 and C-3.

引用

页码：8010 / 8015

页数：6

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