Studies on the Total Synthesis of Natural Alkaloid 6-exo-(Acetyoxy)-8-azabicyclo [3.2.1] octan-2-exo-ol (Ⅱ)——The Synthesis of an Intermediate, 8-Methyl-2β-hydroxy-8-azabicyclo [3.2.1] octane-6-exo carbonitrile

Chem. J. Chinese Universities ›› 1998, Vol. 19 ›› Issue (5): 737.

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Studies on the Total Synthesis of Natural Alkaloid 6-exo-(Acetyoxy)-8-azabicyclo [3.2.1] octan-2-exo-ol (Ⅱ)——The Synthesis of an Intermediate, 8-Methyl-2β-hydroxy-8-azabicyclo [3.2.1] octane-6-exo carbonitrile

ZENG Long-Mei, YANG Shan-Miao, SU Jing-Yu, WU Jian-Qing, WAN Yi-Qian

Department of Chemistry, Zhongshan University, Guangzhou, 510275

Received:1997-04-05 Online:1998-05-24 Published:1998-05-24

Abstract

Abstract: The reaction of N-methyl-3-hydroxypyridinium iodide with acrylonitrile has been studied. Under various reaction conditions, none of the desired cycloaddition product was resulted. Instead, a Michael addition product was obtained. Alternatively, the 1,3-dipolar cycloaddition was achieved by the reaction of N-methyl-3-oxopyridinium betaine with acrylonitrile in THF with a high regioselectivity and stereoselectivity. This paper reports the synthesis of an intermediate 8-methyl-2-β-hydroxy-8-azabicyclo [3.2.1] octane-6-exo-carbonitrile of 6-exo-(acetyoxy)-8-azabicyclo [3.2.1]-octan-2-exo-ol. This synthetic route involves two high stereoselective steps.

Key words: 6-exo-(Acetyoxy)-8-azabicyclo[3.2.1]-octan-2-exo-ol, 1,3-Dipolar cycloaddition, Synthesis, 8-Methyl-2-β-hydroxy-8-azabicyclo[3.2.1]octane-6-exo-carbonitrile

CLC Number:

O624.32

TrendMD:

ZENG Long-Mei, YANG Shan-Miao, SU Jing-Yu, WU Jian-Qing, WAN Yi-Qian . Studies on the Total Synthesis of Natural Alkaloid 6-exo-(Acetyoxy)-8-azabicyclo [3.2.1] octan-2-exo-ol (Ⅱ)——The Synthesis of an Intermediate, 8-Methyl-2β-hydroxy-8-azabicyclo [3.2.1] octane-6-exo carbonitrile[J]. Chem. J. Chinese Universities, 1998, 19(5): 737.

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Studies on the Total Synthesis of Natural Alkaloid 6-exo-(Acetyoxy)-8-azabicyclo [3.2.1] octan-2-exo-ol (Ⅱ)——The Synthesis of an Intermediate, 8-Methyl-2β-hydroxy-8-azabicyclo [3.2.1] octane-6-exo carbonitrile

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