Asymmetric Total Syntheses of (-)-Penicipyrone and (-)-Tenuipyrone via Biomimetic Cascade Intermolecular Michael Addition/Cycloketalization

被引：48

作者：

Song, Liyan ^{[1
]}

Yao, Hongliang ^{[1
]}

Zhu, Liangyu ^{[1
]}

Tong, Rongbiao ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 01期

关键词：

MEDIATED COUPLING REACTIONS; NATURAL-PRODUCT SYNTHESIS; ALPHA; BETA-UNSATURATED KETONES; REACTIVITY; 4-HYDROXY-6-METHYL-2-PYRONE; DERIVATIVES; CHEMISTRY; ALDEHYDES; FUNGUS;

D O I：

10.1021/ol303071t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total syntheses of (-)-penicipyrone and (-)-tenulpyrone were accomplished enantioselectively in 12 steps with an 11% yield and 6 steps with a 28% yield from the known 4-((tert-butyldimethylsilyl)oxy)-cyclopent-2-enone, respectively, by developing a biomimetic bimolecular cascade cyclization featuring an intermolecular Michael addition/cyclo-(spiro-)ketalization sequence. The relative, absolute stereochemistry and carbon connectivity of penicipyrone was further confirmed by X-ray crystallographic analysis and comparison of optical rotations.

引用

页码：6 / 9

页数：4

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