A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

被引：31

作者：

Brandi, A

Cicchi, S

Paschetta, V

Pardo, DG

Cossy, J

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, Italy

[2] ESPCI, CNRS, Chim Organ Lab, F-75231 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 51期

关键词：

C-2; symmetry; 1,3-dipolar cycloaddition; nitrone; indolizidinone;

D O I：

10.1016/S0040-4039(02)02336-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：9357 / 9359

页数：3

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