Total Synthesis of Laingolide B Stereoisomers and Assignment of Absolute Configuration

被引：15

作者：

Cui, Chengsen ^{[1
]}

Dai, Wei-Min ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Lab Adv Catalysis & Synth, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 11期

关键词：

CROSS-COUPLING REACTION; PRACTICAL CHIRAL AUXILIARY; LYNGBYA-BOUILLONII; NATURAL-PRODUCTS; MARINE CYANOBACTERIA; PALMYROLIDE; MACROLIDE; PSEUDOEPHEDRINE; STEREOCHEMISTRY; METATHESIS;

D O I：

10.1021/acs.orglett.8b01269

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of (-)-(2R,9S)- and (+)-(2S,9S)-stereoisomers of laingolide B has been accomplished by using sequential ring-closing metathesis (RCM) and alkene isomerization to construct the macrocyclic trans-N-methyl enamide moiety. The Myers alkylation was used to secure the C2 stereochemistry of the two RCM precursors from a common (9S)-C3-C9 alkyl iodide. The absolute configuration of laingolide B has been assigned as (2S,9R) by comparison of the optical rotation data.

引用

页码：3358 / 3361

页数：4

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