From (-)-quinic acid to 8-azabicyclo[3.2.1]octane framework:: Preparation of an enantiopure tropan-6α-ol

被引：13

作者：

Barco, A

Benetti, S

De Risi, C

Marchetti, P

Pollini, GP

Zanirato, V

机构：

[1] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy

[2] Univ Ferrara, Dipartmento Chim, I-44100 Ferrara, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(99)00254-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The carbon atom ring-insertion via pyrolysis of an alpha-diazo-beta-hydroxy ester intermediate, in turn obtained by reaction between ethyldiazoacetate and 3,4-O-isopropylidene-3(R),4(S)-dihydroxycyclohexanone 2, a chiron easily prepared through a five step sequence from D(-)-quinic acid 1, was the key step for the construction of the cycloheptanone derivative 8. Its transformation into azidosulfate 18 set the stage for the preparation of the N-protected 8-azabicyclo[3.2.1]octane derivative 22, which, to the best of our knowledge, has been never obtained in optically pure form, as well as the tropan-6 alpha-ol 24, obtained by reduction with LiAlH4. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：5923 / 5930

页数：8

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