A convergent synthesis of the cardenolide skeleton:: Intramolecular aldol condensation via reduction of α-bromoketones

被引：40

作者：

Chapdelaine, D ^{[1
]}

Belzile, J ^{[1
]}

Deslongchamps, P ^{[1
]}

机构：

[1] Univ Sherbrooke, Organ Synth Lab, Dept Chim, Inst Pharmacol, Sherbrooke, PQ J1H 5N4, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 16期

关键词：

D O I：

10.1021/jo025612b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of the highly biologically valuable cardenolide backbone was achieved via anionic polycyclization. Bromoketone 18, obtained from double-Michael cycloaddition between cyclohexenone 14 and gamma,delta-unsaturated beta-ketoester 16, was efficiently aldolized under reductive conditions. The highly functionalized tetracyclic compound 52 is an important synthetic intermediate that is potentially amenable to natural cardenolide total synthesis.

引用

页码：5669 / 5672

页数：4

共 26 条

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