Cleavage of (–)‐Eschscholtzine with Sodium in Liquid Ammonia

Lee, Shoei‐Sheng; Lin, Chia-Yin; Chen, Chung‐Hsiung

doi:10.1002/jccs.199100066

J Chinese Chemical Soc

1991

DOI: 10.1002/jccs.199100066

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Cleavage of (–)‐Eschscholtzine with Sodium in Liquid Ammonia

Shoei‐Sheng Lee

Chia-Yin Lin

Chung‐Hsiung Chen

Abstract: (–)‐Eschscholtzine was cleaved with sodium in liquid ammonia to yield 2,8‐dihydroxy‐N‐methylpavine and 2,9‐dihydroxy‐N‐methylpavine. This reaction indicates regioselectivity by cleavage mainly at a site para to the methine carbon of a bridgehead.

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1993

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Cited by 2 publications

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Reinvestigation of the Cleavage of Canadine, A Protoberberine Bearing a Methylenedioxy Function, with Sodium in Liquid Ammonia

Lee¹,

Lee²,

Lin³

et al. 1992

J Chinese Chemical Soc

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Two products, 3‐hydroxy‐9,10‐dimethoxyprotoberberine and 3,9‐dihydroxy‐10‐methoxyprotoberberine in addition to those reported, 2‐hydroxy‐9,10‐dimethoxyprotoberberine and 2,9‐dihydroxy‐10‐methoxyprotoberberine, were identified from cleavage of canadine with sodium in liquid ammonia. This reaction indicates regioselectivity rather than the reported regiospecificity by cleavage mainly at a site para to the N‐methine carbon.

show abstract

Reinvestigation of the Cleavage of Canadine, A Protoberberine Bearing a Methylenedioxy Function, with Sodium in Liquid Ammonia

Lee¹,

Lee²,

Lin³

et al. 1992

J Chinese Chemical Soc

View full text Add to dashboard Cite

show abstract

β-Phenylethylamines and the isoquinoline alkaloids

Bentley¹

1993

Nat. Prod. Rep.

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Cleavage of (–)‐Eschscholtzine with Sodium in Liquid Ammonia

Abstract: (–)‐Eschscholtzine was cleaved with sodium in liquid ammonia to yield 2,8‐dihydroxy‐N‐methylpavine and 2,9‐dihydroxy‐N‐methylpavine. This reaction indicates regioselectivity by cleavage mainly at a site para to the methine carbon of a bridgehead.

Cited by 2 publications

References 4 publications

Reinvestigation of the Cleavage of Canadine, A Protoberberine Bearing a Methylenedioxy Function, with Sodium in Liquid Ammonia

Reinvestigation of the Cleavage of Canadine, A Protoberberine Bearing a Methylenedioxy Function, with Sodium in Liquid Ammonia

β-Phenylethylamines and the isoquinoline alkaloids

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