Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine

被引：6

作者：

Tasic, Gordana ^{[1
]}

Maslak, Veselin ^{[2
]}

Husinec, Suren ^{[3
]}

Todorovic, Nina ^{[3
]}

Savic, Vladimir ^{[1
]}

机构：

[1] Univ Belgrade, Fac Pharm, Dept Organ Chem, Belgrade 11000, Serbia

[2] Univ Belgrade, Fac Chem, Belgrade 11000, Serbia

[3] Inst Chem Technol & Met, Belgrade 11000, Serbia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 19期

关键词：

Heck reaction; Corialstonidine; Bicyclic ketone; ARYLBORONIC ACIDS; HYBRID MOLECULES; ASYMMETRIC HECK; RING-SYSTEM; ELIMINATION; ALKALOIDS; INVERSION; ALDEHYDES; KETONES;

D O I：

10.1016/j.tetlet.2015.03.129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2529 / 2532

页数：4

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