Asymmetric total synthesis of PDIM A:: A virulence factor of Mycobacterium tuberculosis

被引：26

作者：

Casas-Arce, Eva ^{[1
]}

ter Horst, Bjorn ^{[1
]}

Feringa, Ben L. ^{[1
]}

Minnaard, Adriaan J. ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 14期

关键词：

conjugate addition; alkyne addition; asymmetric synthesis; hydrosilylation; mycobacterium tuberculosis;

D O I：

10.1002/chem.200800243

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric synthesis of phthiocerol was achieved in 15 simple steps and 5.6% overall yield by applying three efficient catalytic transformations. The construction of building block 4 started with the copper/phosphoramidite-catalyzed asymmetric conjugate addition of Me 2Zn to cycloheptenone, followed by in situ ethylation. Baeyer Villiger oxidation using excess m-chloroperoxybenzoic acid (mCPBA) followed by treatment of the resulting lactone 7 with K2C03 in MeOH led to the formation of the linear product. Treatment with TBAF followed by a Fleming-Tamao oxidation using KHCO3 and H2O2, resulted in the formation of the corresponding hydroxy ketones, which could be separated by column chromatography affording 16 as a pure isomers.

引用

页码：4157 / 4159

页数：3

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