Total Enantioselective Synthesis of the Endophytic Fungal Polyketide Phomolide H and Its Structural Revision

被引：7
|
作者：
McNulty, James [1 ]
McLeod, David [1 ]
机构：
[1] McMaster Univ, Dept Chem & Chem Biol, 1280 Main St West, Hamilton, ON L8S 4M1, Canada
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 01期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Polyketides; Asymmetric synthesis; Nonenolides; Total synthesis; Macrolactones; STEREOSELECTIVE TOTAL-SYNTHESIS; ACETATE ALDOL REACTIONS; CHOLESTEROL-BIOSYNTHESIS; PHYTOTOXIC NONENOLIDE; (-)-DECARESTRICTINE D; ASYMMETRIC-SYNTHESIS; PHOMA-HERBARUM; LACTONES; (+)-SEIMATOPOLIDE; PINOLIDOXIN;
D O I：
10.1002/ejoc.201601172
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A total synthesis of the proposed structure of the natural polyketide-macrolactone phomolide H 2 has been achieved following a bidirectional strategy from L-tartaric acid. The originally assigned structure of phomolide H displayed discordant NMR spectroscopic data in comparison with synthetic 2. The synthetic strategy was extended to prepare diastereomers and epimeric methyl-ethers of the natural product, structural analysis of which revealed a match of the natural product with diastereomer 27. The structural revision of phomolide H from 2 to the methanol solvate of compound 27 is presented.
引用
收藏
页码：29 / 33
页数：5
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