Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol

被引：29

作者：

Das, Subhendu ^{[1
]}

Kuilya, Tapan Kumar ^{[1
]}

Goswami, Rajib Kumar ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 12期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; WACKER OXIDATION; FORMAL SYNTHESIS; DIHYDROXYLATION; CONDENSATION; DERIVATIVES; ALDEHYDES; EPOXIDES; SULFONES; REVISION;

D O I：

10.1021/acs.joc.5b00972

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and convergent route for stereoselective total synthesis of promising anticancer natural lipid mycalol has been achieved using cheap and readily available L-arabinose as a chiral pool. The notable features of our synthesis comprised regioselective Wacker oxidation, Sharpless asymmetric dihydroxylation, Julia-Kocienski olefination, Wittig olefination, Zipper reaction, and Sonogashira reaction. Comparison of the spectroscopic data on a series of isomers supports the revised structure (Org. Lett. 2015, 17, 1652) instead of the one originally proposed.

引用

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页码：6467 / 6489

页数：23

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