NEW METHODS AND STRATEGIES FOR THE STEREOCONTROLLED SYNTHESIS OF POLYPROPIONATE-DERIVED NATURAL-PRODUCTS

被引：96

作者：

PATERSON, I

机构：

[1] University Chemical Laboratory, Lensfield Road, Cambridge

来源：

PURE AND APPLIED CHEMISTRY | 1992年 / 64卷 / 12期

关键词：

D O I：

10.1351/pac199264121821

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By using the stereoregulated aldol reactions of chiral enol borinates with aldehydes, the synthesis of elaborate segments of polypropionate-derived natural products can be readily achieved. Stereocontrol may originate from the chiral influence of the boron reagent, the starting ketone (dependent on substitution pattern and enol borinate geometry), and the aldehyde, or from some combination of these (multiple asymmetric induction). Subsequent elaboration of the beta-hydroxy ketone adducts can then be performed with a high level of overall diastereoselectivity. Examples of these reactions are given in the context of the synthesis of various polypropionate-derived natural products, including antibiotics (oleandomycin, rifamycin S), antitumour agents (swinholide A), enzyme inhibitors (ebelactone A), and marine polypropionates (denticulatin A and B).

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页码：1821 / 1830

页数：10

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