Stereochemically Versatile Synthesis of the C1-C12 Fragment of Tedanolide C

被引：19

作者：

Smith, Thomas E. ^{[1
]}

Fink, Sarah J. ^{[1
]}

Levine, Zebulon G. ^{[1
]}

McClelland, Kerani A. ^{[1
]}

Zackheim, Adrian A. ^{[1
]}

Daub, Mary E. ^{[1
]}

机构：

[1] Williams Coll, Dept Chem, Williamstown, MA 01267 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 06期

关键词：

ASYMMETRIC HYDROFORMYLATION; STEREOSELECTIVE-SYNTHESIS; ANTITUMOR MACROLIDE; RIBOSOMAL-SUBUNIT; (+)-13-DEOXYTEDANOLIDE; (+)-TEDANOLIDE; 13-DEOXYTEDANOLIDE; POLYKETIDE; REDUCTION; LIGANDS;

D O I：

10.1021/ol300194x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A flexible synthesis of the C1-C12 fragment of Tedanolide C has been accomplished in eight steps from 2-methyl-2,4-pentadienal. Asymmetric hydroformylation of a 1,3-diene allows for the late-stage generation of either C10 epimer with complete catalyst control. Diastereoselective addition of an isobutyryl beta-ketoester dianion to an alpha,beta-disubstituted chiral aldehyde sets the C5 stereochemistry while installing the geminal dimethyl unit. Differential protection of a syn-1,3-diol is performed as a highly efficient single-pot operation.

引用

页码：1452 / 1455

页数：4

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