A new approach to the pancratistatin C-ring from D-glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

被引：16

作者：

Friestad, GK ^{[1
]}

Branchaud, BP ^{[1
]}

机构：

[1] UNIV OREGON,DEPT CHEM,EUGENE,OR 97403

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 34期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(97)01325-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Ferrier rearrangement and beta-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by beta-hydroxyketone transposition, which allows convenient access from methyl alpha-D-glucopyranoside Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the Cl hydroxyl to deliver the tethered aryl synthon. (C) 1997 Elsevier Science Ltd.

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收藏

页码：5933 / 5936

页数：4

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