Highly Stereoselective Aldol Reactions in the Total Syntheses of Complex Natural Products

被引：100

作者：

Brodmann, Tobias ^{[1
]}

Lorenz, Michael ^{[1
]}

Schaeckel, Romy ^{[1
]}

Simsek, Serkan ^{[1
]}

Kalesse, Markus ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

来源：

SYNLETT | 2009年 / 02期

关键词：

aldol reactions; vinylogy; stereoselectivity; natural product synthesis; LEWIS-BASE ACTIVATION; ENANTIOSELECTIVE DIENOLATE ADDITIONS; STEREOCONTROLLED TOTAL-SYNTHESIS; VINYLOGOUS MUKAIYAMA REACTIONS; ASYMMETRIC-SYNTHESIS; ACYCLIC STEREOSELECTION; SORANGIUM-CELLULOSUM; GLIDING BACTERIA; DIASTEREOFACIAL SELECTIVITY; 1,2 DIASTEREOSELECTION;

D O I：

10.1055/s-0028-1087520

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

More than ever, it is a challenging objective in synthetic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated in the framework of complex natural products is a beta-hydroxy ketone. In this context, the aldol reaction as the most important transformation to generate this structural element not only creates new C-C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies for aldol and aldol-type reactions has been put forward. On this background, the vinylogous Mukaiyama aldol reaction became a pivotal transformation since it also allows for the immediate transformation of the olefin which is simultaneously introduced. This Account covers the application of various (vinylogous) aldol reactions from our laboratories in the syntheses of natural products with important biological activities.

引用

页码：174 / 192

页数：19

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