Asymmetric syntheses of panclicins A-E via [2+2] cycloaddition of alkyl(trimethylsilyl)ketenes to a β-silyloxyaldehyde

被引：22

作者：

Kocienski, PJ ^{[1
]}

Pelotier, B

Pons, JM

Prideaux, H

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] Fac Sci & Tech St Jerome, UMR CNRS 6516, Lab React Synth Organ ReSo, F-13397 Marseille 20, France

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 08期

关键词：

D O I：

10.1039/a800807h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Panclicins A-E, pancreatic lipase inhibitors from Streptomyces, were synthesised in a modular fashion starting with three alkyl(trimethylsilyl)ketenes, two amino acids and a single aldehyde component, (3R)-3-(tert-butyldimethylsilyloxy)decanal 11, The lone stereocentre in 11 which governs the stereochemistry in subsequent steps was generated by Noyori asymmetric hydrogenation. The key step, a Lewis acid catalysed [2+2] cycloaddition of alkyl(trimethylsilyl)ketenes 13a-c to 11, gave three 3-trimethylsilyloxetan-2-ones with good 1,3-asymmetric induction. After C-and O-desilylation the amino acid side chains were introduced using a Mitsunobu inversion.

引用

页码：1373 / 1382

页数：10

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